DE2363458C3 - Aminobenzaldehydverbindungen und ein Verfahren zu ihrer Herstellung - Google Patents
Aminobenzaldehydverbindungen und ein Verfahren zu ihrer HerstellungInfo
- Publication number
- DE2363458C3 DE2363458C3 DE2363458A DE2363458A DE2363458C3 DE 2363458 C3 DE2363458 C3 DE 2363458C3 DE 2363458 A DE2363458 A DE 2363458A DE 2363458 A DE2363458 A DE 2363458A DE 2363458 C3 DE2363458 C3 DE 2363458C3
- Authority
- DE
- Germany
- Prior art keywords
- radical
- aliphatic
- acid
- parts
- araliphatic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 17
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical class NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 15
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 150000004820 halides Chemical class 0.000 claims description 12
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 4
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 4
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000003948 formamides Chemical class 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 3
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- -1 alkyl anilines Chemical class 0.000 description 27
- 239000007858 starting material Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
- 150000003254 radicals Chemical class 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 14
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FEOIEIQLXALHPJ-UHFFFAOYSA-N 3-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=CC(C#N)=C1 FEOIEIQLXALHPJ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 125000004430 oxygen atom Chemical group O* 0.000 description 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- DHLFXZQEAWYQLC-UHFFFAOYSA-N 4-(dimethylamino)-2-nitrobenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C([N+]([O-])=O)=C1 DHLFXZQEAWYQLC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CUFNKYGDVFVPHO-UHFFFAOYSA-N Azulene Natural products C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000005874 Vilsmeier-Haack formylation reaction Methods 0.000 description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- CJDICMLSLYHRPT-UHFFFAOYSA-N n,n-dimethyl-3-nitroaniline Chemical compound CN(C)C1=CC=CC([N+]([O-])=O)=C1 CJDICMLSLYHRPT-UHFFFAOYSA-N 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 3
- 229940067157 phenylhydrazine Drugs 0.000 description 3
- LIZLYZVAYZQVPG-UHFFFAOYSA-N (3-bromo-2-fluorophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1F LIZLYZVAYZQVPG-UHFFFAOYSA-N 0.000 description 2
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- OAGBEOHRGRUDEO-UHFFFAOYSA-N 3-(dimethylamino)benzamide Chemical compound CN(C)C1=CC=CC(C(N)=O)=C1 OAGBEOHRGRUDEO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000981 basic dye Substances 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- KOWLGQIEEVQBKZ-UHFFFAOYSA-N methyl 5-(dimethylamino)-2-formylbenzoate Chemical compound COC(=O)C1=CC(N(C)C)=CC=C1C=O KOWLGQIEEVQBKZ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- QSNHMSRICSDACJ-UHFFFAOYSA-N n,n-diethyl-3-nitroaniline Chemical compound CCN(CC)C1=CC=CC([N+]([O-])=O)=C1 QSNHMSRICSDACJ-UHFFFAOYSA-N 0.000 description 2
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- ANMVHJPIGPTCSG-UHFFFAOYSA-N 1-nitroazulene Chemical compound C1=CC=CC=C2C([N+](=O)[O-])=CC=C21 ANMVHJPIGPTCSG-UHFFFAOYSA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GWDBNEGVXKROFM-UHFFFAOYSA-N 3-(diethylamino)benzonitrile Chemical compound CCN(CC)C1=CC=CC(C#N)=C1 GWDBNEGVXKROFM-UHFFFAOYSA-N 0.000 description 1
- YLEQLDTWPAPPGF-UHFFFAOYSA-N 4-(dibenzylamino)-2-nitrobenzaldehyde Chemical compound C1=C(C=O)C([N+](=O)[O-])=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 YLEQLDTWPAPPGF-UHFFFAOYSA-N 0.000 description 1
- YQJLRLBMMHSMOA-UHFFFAOYSA-N 4-(diethylamino)-2-nitrobenzaldehyde Chemical compound CCN(CC)C1=CC=C(C=O)C([N+]([O-])=O)=C1 YQJLRLBMMHSMOA-UHFFFAOYSA-N 0.000 description 1
- KMIFZPQZABQRBA-UHFFFAOYSA-N 4-(dimethylamino)-2-nitrobenzaldehyde (4-methylphenyl)diazene Chemical compound CC1=CC=C(N=N)C=C1.CN(C)C1=CC=C(C=O)C([N+]([O-])=O)=C1 KMIFZPQZABQRBA-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- BTOJSYRZQZOMOK-UHFFFAOYSA-N 4-chloro-7-(4-methylphenyl)sulfonylpyrrolo[2,3-d]pyrimidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C2=NC=NC(Cl)=C2C=C1 BTOJSYRZQZOMOK-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- SLMBJRUTIPGBJQ-UHFFFAOYSA-N 5-(dimethylamino)-2-formylbenzonitrile Chemical compound CN(C)C1=CC=C(C=O)C(C#N)=C1 SLMBJRUTIPGBJQ-UHFFFAOYSA-N 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- WHOWEWJMRFCYOS-UHFFFAOYSA-N N,N-dimethyl-3-nitro-4-[(phenylhydrazinylidene)methyl]aniline Chemical compound [O-][N+](=O)C1=CC(N(C)C)=CC=C1C=NNC1=CC=CC=C1 WHOWEWJMRFCYOS-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001545 azulenes Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- QNCMDFVHPFYZNK-UHFFFAOYSA-N butan-1-ol;2-methylpropan-1-ol Chemical compound CCCCO.CC(C)CO QNCMDFVHPFYZNK-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- JNUPSMNVNNYRAI-UHFFFAOYSA-N cyclohexyl 3-aminobenzoate Chemical compound NC1=CC=CC(C(=O)OC2CCCCC2)=C1 JNUPSMNVNNYRAI-UHFFFAOYSA-N 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- DASKKRDHXATCCX-UHFFFAOYSA-N ethyl 3-(diethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC(N(CC)CC)=C1 DASKKRDHXATCCX-UHFFFAOYSA-N 0.000 description 1
- CWYCOEUFVMVJQF-UHFFFAOYSA-N ethyl 5-(dimethylamino)-2-formylbenzoate Chemical compound CCOC(=O)C1=CC(N(C)C)=CC=C1C=O CWYCOEUFVMVJQF-UHFFFAOYSA-N 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GHDIHPNJQVDFBL-UHFFFAOYSA-N methoxycyclohexane Chemical compound COC1CCCCC1 GHDIHPNJQVDFBL-UHFFFAOYSA-N 0.000 description 1
- CABFTHPIDKWPNQ-UHFFFAOYSA-N methyl 3-(dimethylamino)benzoate Chemical compound COC(=O)C1=CC=CC(N(C)C)=C1 CABFTHPIDKWPNQ-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DRBODBSEJPJTGK-UHFFFAOYSA-N n,n-dibenzyl-3-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=C1 DRBODBSEJPJTGK-UHFFFAOYSA-N 0.000 description 1
- KDDAADQPHACPQC-UHFFFAOYSA-N n,n-dibutyl-3-nitroaniline Chemical compound CCCCN(CCCC)C1=CC=CC([N+]([O-])=O)=C1 KDDAADQPHACPQC-UHFFFAOYSA-N 0.000 description 1
- PYHIRJVZBQENPL-UHFFFAOYSA-N n-(2,2-dichloroethyl)-3-nitroaniline Chemical compound [O-][N+](=O)C1=CC=CC(NCC(Cl)Cl)=C1 PYHIRJVZBQENPL-UHFFFAOYSA-N 0.000 description 1
- ZOAPFKLJEWIJGZ-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)-3-nitroaniline Chemical compound COC(OC)CNC1=CC=CC([N+]([O-])=O)=C1 ZOAPFKLJEWIJGZ-UHFFFAOYSA-N 0.000 description 1
- XCTTVNSXEHWZBI-UHFFFAOYSA-N n-(2-methylpropyl)formamide Chemical compound CC(C)CNC=O XCTTVNSXEHWZBI-UHFFFAOYSA-N 0.000 description 1
- PRECPUSKWZCRQZ-UHFFFAOYSA-N n-[[4-(dimethylamino)-2-nitrophenyl]methylidene]hydroxylamine Chemical compound CN(C)C1=CC=C(C=NO)C([N+]([O-])=O)=C1 PRECPUSKWZCRQZ-UHFFFAOYSA-N 0.000 description 1
- IHQBWCMBIMXLCF-UHFFFAOYSA-N n-benzyl-n-methyl-3-nitroaniline Chemical compound C=1C=CC([N+]([O-])=O)=CC=1N(C)CC1=CC=CC=C1 IHQBWCMBIMXLCF-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- VATYWCRQDJIRAI-UHFFFAOYSA-N p-aminobenzaldehyde Chemical class NC1=CC=C(C=O)C=C1 VATYWCRQDJIRAI-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 150000008379 phenol ethers Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VYWALUQMDDJGMZ-UHFFFAOYSA-N propan-2-yl 3-(dipropylamino)benzoate Chemical compound CCCN(CCC)C1=CC=CC(C(=O)OC(C)C)=C1 VYWALUQMDDJGMZ-UHFFFAOYSA-N 0.000 description 1
- MINHQZSOIGYJHE-UHFFFAOYSA-N propan-2-yl 5-(dimethylamino)-2-formylbenzoate Chemical compound CC(C)OC(=O)C1=CC(N(C)C)=CC=C1C=O MINHQZSOIGYJHE-UHFFFAOYSA-N 0.000 description 1
- MRFWEYWNLJMKCC-UHFFFAOYSA-N propyl 5-(dimethylamino)-2-formylbenzoate Chemical compound CCCOC(=O)C1=CC(N(C)C)=CC=C1C=O MRFWEYWNLJMKCC-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
- 150000004961 triphenylmethanes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Coloring (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2363458A DE2363458C3 (de) | 1973-12-20 | 1973-12-20 | Aminobenzaldehydverbindungen und ein Verfahren zu ihrer Herstellung |
| US05/531,090 US3971821A (en) | 1973-12-20 | 1974-12-09 | Production of aminobenzaldehydes |
| FR7440791A FR2255289B3 (OSRAM) | 1973-12-20 | 1974-12-11 | |
| CH1674574A CH609333A5 (OSRAM) | 1973-12-20 | 1974-12-17 | |
| GB54592/74A GB1483248A (en) | 1973-12-20 | 1974-12-18 | Aminobenzaldehyde compounds and derivatives and a process for their production |
| JP49144596A JPS5095235A (OSRAM) | 1973-12-20 | 1974-12-18 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2363458A DE2363458C3 (de) | 1973-12-20 | 1973-12-20 | Aminobenzaldehydverbindungen und ein Verfahren zu ihrer Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2363458A1 DE2363458A1 (de) | 1975-07-03 |
| DE2363458B2 DE2363458B2 (de) | 1980-10-23 |
| DE2363458C3 true DE2363458C3 (de) | 1981-09-03 |
Family
ID=5901362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2363458A Expired DE2363458C3 (de) | 1973-12-20 | 1973-12-20 | Aminobenzaldehydverbindungen und ein Verfahren zu ihrer Herstellung |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3971821A (OSRAM) |
| JP (1) | JPS5095235A (OSRAM) |
| CH (1) | CH609333A5 (OSRAM) |
| DE (1) | DE2363458C3 (OSRAM) |
| FR (1) | FR2255289B3 (OSRAM) |
| GB (1) | GB1483248A (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4176198A (en) * | 1977-10-06 | 1979-11-27 | William H. Rorer, Inc. | Method of treatment |
| US4150987A (en) * | 1977-10-17 | 1979-04-24 | International Business Machines Corporation | Hydrazone containing charge transport element and photoconductive process of using same |
| US4399291A (en) * | 1981-12-09 | 1983-08-16 | Sterling Drug Inc. | Process for the production of substituted aminophthalides |
| US4528136A (en) * | 1981-12-09 | 1985-07-09 | The Hilton-Davis Chemical Co. | Process for preparing 2-[bis(aryl)methyl]benzoic acids |
| US4857071A (en) * | 1987-08-21 | 1989-08-15 | Clairol, Inc. | Novel hair dye and method of use |
| US4900859A (en) * | 1987-12-03 | 1990-02-13 | Hoffman-La Roche Inc. | Process for 4-dimethylamino-3,5-dimethoxybenzaldehyde |
| US5225577A (en) * | 1989-04-28 | 1993-07-06 | Naoya Ogata | Organic nonlinear optical material |
| EP0634404A1 (en) * | 1993-07-13 | 1995-01-18 | Rhone Poulenc Agriculture Ltd. | Phtalazin derivatives and their use as pesticides |
| CN102010344A (zh) * | 2010-10-11 | 2011-04-13 | 南开大学 | 邻氨基苯甲醛的一种稳定衍生物的合成方法 |
-
1973
- 1973-12-20 DE DE2363458A patent/DE2363458C3/de not_active Expired
-
1974
- 1974-12-09 US US05/531,090 patent/US3971821A/en not_active Expired - Lifetime
- 1974-12-11 FR FR7440791A patent/FR2255289B3/fr not_active Expired
- 1974-12-17 CH CH1674574A patent/CH609333A5/xx not_active IP Right Cessation
- 1974-12-18 GB GB54592/74A patent/GB1483248A/en not_active Expired
- 1974-12-18 JP JP49144596A patent/JPS5095235A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US3971821A (en) | 1976-07-27 |
| DE2363458A1 (de) | 1975-07-03 |
| GB1483248A (en) | 1977-08-17 |
| DE2363458B2 (de) | 1980-10-23 |
| CH609333A5 (OSRAM) | 1979-02-28 |
| JPS5095235A (OSRAM) | 1975-07-29 |
| FR2255289A1 (OSRAM) | 1975-07-18 |
| FR2255289B3 (OSRAM) | 1977-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |