DE2454356A1 - 2-(gamma-aminopropyl)-hydrochinon und zwischenprodukte hierfuer sowie verfahren zur herstellung derselben - Google Patents
2-(gamma-aminopropyl)-hydrochinon und zwischenprodukte hierfuer sowie verfahren zur herstellung derselbenInfo
- Publication number
- DE2454356A1 DE2454356A1 DE19742454356 DE2454356A DE2454356A1 DE 2454356 A1 DE2454356 A1 DE 2454356A1 DE 19742454356 DE19742454356 DE 19742454356 DE 2454356 A DE2454356 A DE 2454356A DE 2454356 A1 DE2454356 A1 DE 2454356A1
- Authority
- DE
- Germany
- Prior art keywords
- aminopropyl
- derivative
- benzene ring
- additional substituents
- acid
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000004519 manufacturing process Methods 0.000 title description 8
- 239000013067 intermediate product Substances 0.000 title description 2
- 125000001424 substituent group Chemical group 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 20
- -1 γ-aminopropyl Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 11
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 10
- 150000005224 alkoxybenzenes Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- VBHNZUGUQZKOOE-UHFFFAOYSA-N 2-(3-aminopropyl)benzene-1,4-diol Chemical compound NCCCC1=CC(O)=CC=C1O VBHNZUGUQZKOOE-UHFFFAOYSA-N 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- 230000020335 dealkylation Effects 0.000 claims description 6
- 238000006900 dealkylation reaction Methods 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 238000006114 decarboxylation reaction Methods 0.000 claims description 4
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- OMSBSIXAZZRIRW-UHFFFAOYSA-N 2-methylpyridine;hydrochloride Chemical compound Cl.CC1=CC=CC=N1 OMSBSIXAZZRIRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000000543 intermediate Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-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
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
- AFUKNJHPZAVHGQ-UHFFFAOYSA-N 2,5-dimethoxy-Benzaldehyde Chemical compound COC1=CC=C(OC)C(C=O)=C1 AFUKNJHPZAVHGQ-UHFFFAOYSA-N 0.000 description 3
- XDCGVZXQMCGIIF-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)prop-2-enenitrile Chemical compound COC1=CC=C(OC)C(C=CC#N)=C1 XDCGVZXQMCGIIF-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- TYWAQPHUBWNPMP-UHFFFAOYSA-N 2-(2-aminopropyl)benzene-1,4-diol Chemical compound CC(N)CC1=CC(O)=CC=C1O TYWAQPHUBWNPMP-UHFFFAOYSA-N 0.000 description 2
- RTBLTCFCRGIGFB-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)propan-1-amine Chemical compound COC1=CC=C(OC)C(CCCN)=C1 RTBLTCFCRGIGFB-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SWHVIJVKHBFUBI-UHFFFAOYSA-N 2-(3-aminopropyl)-3-bromobenzene-1,4-diol Chemical compound NCCCC1=C(O)C=CC(O)=C1Br SWHVIJVKHBFUBI-UHFFFAOYSA-N 0.000 description 1
- BQKSTIMTRFPXMR-UHFFFAOYSA-N 2-(3-aminopropyl)benzene-1,4-diol;hydrobromide Chemical compound Br.NCCCC1=CC(O)=CC=C1O BQKSTIMTRFPXMR-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- RJEMPQIDYIIZPG-UHFFFAOYSA-N 3-(2,5-diethoxy-3-methylphenyl)propan-1-amine Chemical compound CCOC1=CC(C)=C(OCC)C(CCCN)=C1 RJEMPQIDYIIZPG-UHFFFAOYSA-N 0.000 description 1
- UTRNGBINFHKARA-UHFFFAOYSA-N 3-(2,5-diethoxyphenyl)prop-2-enenitrile Chemical compound CCOC1=CC=C(OCC)C(C=CC#N)=C1 UTRNGBINFHKARA-UHFFFAOYSA-N 0.000 description 1
- OYTNTHOAIYTRTM-UHFFFAOYSA-N 3-(2,5-dimethoxy-3-methylphenyl)propan-1-amine Chemical compound COC1=CC(C)=C(OC)C(CCCN)=C1 OYTNTHOAIYTRTM-UHFFFAOYSA-N 0.000 description 1
- PJNFODDKCDCQKE-UHFFFAOYSA-N 3-(2-bromo-3,6-diethoxyphenyl)prop-2-enenitrile Chemical compound CCOC1=CC=C(OCC)C(C=CC#N)=C1Br PJNFODDKCDCQKE-UHFFFAOYSA-N 0.000 description 1
- RJJRBEPVVVZWAB-UHFFFAOYSA-N 3-(2-bromo-3,6-dimethoxyphenyl)prop-2-enenitrile Chemical compound COC1=CC=C(OC)C(C=CC#N)=C1Br RJJRBEPVVVZWAB-UHFFFAOYSA-N 0.000 description 1
- SVXDUJKRPYHPST-UHFFFAOYSA-N 3-(2-bromo-3,6-dimethoxyphenyl)propan-1-amine Chemical compound COC1=CC=C(OC)C(CCCN)=C1Br SVXDUJKRPYHPST-UHFFFAOYSA-N 0.000 description 1
- RXUHKHAFHPTSBU-UHFFFAOYSA-N 3-(3-bromo-2,5-diethoxyphenyl)prop-2-enenitrile Chemical compound CCOC1=CC(Br)=C(OCC)C(C=CC#N)=C1 RXUHKHAFHPTSBU-UHFFFAOYSA-N 0.000 description 1
- XMBCINDHLSZQQZ-UHFFFAOYSA-N 3-(3-butyl-2,5-dimethoxyphenyl)propan-1-amine Chemical compound CCCCC1=CC(OC)=CC(CCCN)=C1OC XMBCINDHLSZQQZ-UHFFFAOYSA-N 0.000 description 1
- MGASUUGJVISCHJ-UHFFFAOYSA-N 3-(3-chloro-2,5-diethoxyphenyl)prop-2-enenitrile Chemical compound CCOC1=CC(Cl)=C(OCC)C(C=CC#N)=C1 MGASUUGJVISCHJ-UHFFFAOYSA-N 0.000 description 1
- CZRQCVMGHQQCAW-UHFFFAOYSA-N 3-(3-chloro-2,5-dimethoxyphenyl)prop-2-enenitrile Chemical compound COC1=CC(Cl)=C(OC)C(C=CC#N)=C1 CZRQCVMGHQQCAW-UHFFFAOYSA-N 0.000 description 1
- LSVQCFWYTXNJJZ-UHFFFAOYSA-N 3-(3-ethyl-2,5-dimethoxyphenyl)propan-1-amine Chemical compound CCC1=CC(OC)=CC(CCCN)=C1OC LSVQCFWYTXNJJZ-UHFFFAOYSA-N 0.000 description 1
- PYYPHJSPHBWBBO-UHFFFAOYSA-N 3-(3-tert-butyl-2,5-dimethoxyphenyl)prop-2-enenitrile Chemical compound COC1=CC(C=CC#N)=C(OC)C(C(C)(C)C)=C1 PYYPHJSPHBWBBO-UHFFFAOYSA-N 0.000 description 1
- DYUDFEGUSXSHFQ-UHFFFAOYSA-N 3-(3-tert-butyl-2,5-dimethoxyphenyl)propan-1-amine Chemical compound COC1=CC(CCCN)=C(OC)C(C(C)(C)C)=C1 DYUDFEGUSXSHFQ-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 235000010724 Wisteria floribunda Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000012380 dealkylating agent Substances 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- ZNSWGHZWUUFFKV-UHFFFAOYSA-N piperidine;pyridine Chemical compound C1CCNCC1.C1=CC=NC=C1 ZNSWGHZWUUFFKV-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000004043 responsiveness Effects 0.000 description 1
- 229920006395 saturated elastomer Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/62—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
- D01D10/00—Physical treatment of artificial filaments or the like during manufacture, i.e. during a continuous production process before the filaments have been collected
- D01D10/06—Washing or drying
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Textile Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742462026 DE2462026A1 (de) | 1973-11-16 | 1974-11-15 | Delta-aminopropyl-2,5-di-niedrig- alkoxybenzole und verfahren zu deren herstellung |
| DE19742462025 DE2462025A1 (de) | 1973-11-16 | 1974-11-15 | Beta-(2,5-di-niedrig-alkoxyphenyl)- acrylnitrile oder derivate hiervon mit zusaetzlichen substituenten am benzolring in der 3-,4-, und'oder 6-stellung sowie verfahren zur herstellung derselben |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP48128987A JPS5077339A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-11-16 | 1973-11-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2454356A1 true DE2454356A1 (de) | 1975-06-26 |
Family
ID=14998309
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742454356 Withdrawn DE2454356A1 (de) | 1973-11-16 | 1974-11-15 | 2-(gamma-aminopropyl)-hydrochinon und zwischenprodukte hierfuer sowie verfahren zur herstellung derselben |
| DE19742462025 Withdrawn DE2462025A1 (de) | 1973-11-16 | 1974-11-15 | Beta-(2,5-di-niedrig-alkoxyphenyl)- acrylnitrile oder derivate hiervon mit zusaetzlichen substituenten am benzolring in der 3-,4-, und'oder 6-stellung sowie verfahren zur herstellung derselben |
| DE19742462026 Withdrawn DE2462026A1 (de) | 1973-11-16 | 1974-11-15 | Delta-aminopropyl-2,5-di-niedrig- alkoxybenzole und verfahren zu deren herstellung |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742462025 Withdrawn DE2462025A1 (de) | 1973-11-16 | 1974-11-15 | Beta-(2,5-di-niedrig-alkoxyphenyl)- acrylnitrile oder derivate hiervon mit zusaetzlichen substituenten am benzolring in der 3-,4-, und'oder 6-stellung sowie verfahren zur herstellung derselben |
| DE19742462026 Withdrawn DE2462026A1 (de) | 1973-11-16 | 1974-11-15 | Delta-aminopropyl-2,5-di-niedrig- alkoxybenzole und verfahren zu deren herstellung |
Country Status (4)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2502740A1 (fr) * | 1981-03-30 | 1982-10-01 | Coutlis Theo | Dispositif electrique pour detection des fuites d'eau |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE570596A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1957-08-26 |
-
1973
- 1973-11-16 JP JP48128987A patent/JPS5077339A/ja active Pending
-
1974
- 1974-11-15 DE DE19742454356 patent/DE2454356A1/de not_active Withdrawn
- 1974-11-15 DE DE19742462025 patent/DE2462025A1/de not_active Withdrawn
- 1974-11-15 GB GB4963574A patent/GB1466459A/en not_active Expired
- 1974-11-15 DE DE19742462026 patent/DE2462026A1/de not_active Withdrawn
- 1974-11-18 US US05/524,836 patent/US3992449A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5077339A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-24 |
| DE2462025A1 (de) | 1976-03-25 |
| DE2462026A1 (de) | 1975-10-02 |
| GB1466459A (en) | 1977-03-09 |
| US3992449A (en) | 1976-11-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |