JPH0556334B2 - - Google Patents
Info
- Publication number
- JPH0556334B2 JPH0556334B2 JP85132089A JP13208985A JPH0556334B2 JP H0556334 B2 JPH0556334 B2 JP H0556334B2 JP 85132089 A JP85132089 A JP 85132089A JP 13208985 A JP13208985 A JP 13208985A JP H0556334 B2 JPH0556334 B2 JP H0556334B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- group
- formula
- ether
- organic solvent
- 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 - Fee Related
Links
- 239000003054 catalyst Substances 0.000 claims description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 19
- -1 trifluoromethyl- Chemical group 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- VYZAHLCBVHPDDF-UHFFFAOYSA-N Dinitrochlorobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 VYZAHLCBVHPDDF-UHFFFAOYSA-N 0.000 claims description 13
- 239000002585 base Substances 0.000 claims description 13
- 239000003495 polar organic solvent Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 238000002955 isolation Methods 0.000 claims description 12
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 11
- 230000003197 catalytic effect Effects 0.000 claims description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- 229910000510 noble metal Inorganic materials 0.000 claims description 9
- 230000029936 alkylation Effects 0.000 claims description 7
- 238000005804 alkylation reaction Methods 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- WGAXJEXVOSVLFY-UHFFFAOYSA-N 1-(2,4-dinitrophenoxy)-2,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC=C1OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O WGAXJEXVOSVLFY-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical group 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000000737 periodic effect Effects 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052697 platinum Inorganic materials 0.000 claims description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229940031826 phenolate Drugs 0.000 claims description 4
- 229910052707 ruthenium Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 16
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 238000005932 reductive alkylation reaction Methods 0.000 description 6
- WZEPMNYUOAOPIK-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)OCC(OC)N Chemical compound C(C)(=O)NC1=CC=C(C=C1)OCC(OC)N WZEPMNYUOAOPIK-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- IFQVEYUAIINTRX-UHFFFAOYSA-N 2-methoxyethoxybenzene Chemical compound COCCOC1=CC=CC=C1 IFQVEYUAIINTRX-UHFFFAOYSA-N 0.000 description 3
- MTNLEKFLKGGTKS-UHFFFAOYSA-N 4-(2,4-diaminophenoxy)benzene-1,3-diamine Chemical compound NC1=CC(N)=CC=C1OC1=CC=C(N)C=C1N MTNLEKFLKGGTKS-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- QRGALPKVWIQXKQ-UHFFFAOYSA-N n-[4-(2-amino-2-methoxyethoxy)phenyl]propanamide Chemical compound CCC(=O)NC1=CC=C(OCC(N)OC)C=C1 QRGALPKVWIQXKQ-UHFFFAOYSA-N 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- SEJFWAWYAJTLJD-UHFFFAOYSA-N 1-(2,3-dinitrophenoxy)-2,3-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(OC=2C(=C(C=CC=2)[N+]([O-])=O)[N+]([O-])=O)=C1[N+]([O-])=O SEJFWAWYAJTLJD-UHFFFAOYSA-N 0.000 description 2
- BAHPQISAXRFLCL-UHFFFAOYSA-N 2,4-Diaminoanisole Chemical compound COC1=CC=C(N)C=C1N BAHPQISAXRFLCL-UHFFFAOYSA-N 0.000 description 2
- CVYZVNVPQRKDLW-UHFFFAOYSA-N 2,4-dinitroanisole Chemical compound COC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O CVYZVNVPQRKDLW-UHFFFAOYSA-N 0.000 description 2
- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 2
- GGVZNGYEHJHVMK-UHFFFAOYSA-N 2-(2-methoxyethoxy)aniline Chemical compound COCCOC1=CC=CC=C1N GGVZNGYEHJHVMK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- BIBOUMJSDFPHJJ-UHFFFAOYSA-N N-[4-[2-(ethylamino)-2-methoxyethoxy]phenyl]propanamide Chemical compound CCNC(OC)COC1=CC=C(NC(=O)CC)C=C1 BIBOUMJSDFPHJJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- XTKBLPKQFBQFTC-UHFFFAOYSA-N n-[3-(ethylamino)-4-methoxyphenyl]acetamide Chemical compound CCNC1=CC(NC(C)=O)=CC=C1OC XTKBLPKQFBQFTC-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
- GOJFAKBEASOYNM-UHFFFAOYSA-N 2-(2-aminophenoxy)aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1N GOJFAKBEASOYNM-UHFFFAOYSA-N 0.000 description 1
- ADHVQCZSFFSNCV-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzene-1,2-diamine Chemical compound COCCOC1=CC=CC(N)=C1N ADHVQCZSFFSNCV-UHFFFAOYSA-N 0.000 description 1
- BFLWXPJTAKXXKT-UHFFFAOYSA-N 3-methoxybenzene-1,2-diamine Chemical compound COC1=CC=CC(N)=C1N BFLWXPJTAKXXKT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003869 coulometry Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 239000000986 disperse dye Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- YNQNTUVMQPQFEW-UHFFFAOYSA-N methyl 2-hydroxyacetate;sodium Chemical compound [Na].COC(=O)CO YNQNTUVMQPQFEW-UHFFFAOYSA-N 0.000 description 1
- SJWQCBCAGCEWCV-UHFFFAOYSA-N n-(3-amino-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1N SJWQCBCAGCEWCV-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- BTJCIVXKBILNPY-UHFFFAOYSA-N n-[3-(diethylamino)-4-methoxyphenyl]acetamide Chemical compound CCN(CC)C1=CC(NC(C)=O)=CC=C1OC BTJCIVXKBILNPY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/84—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
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)
Description
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3422809 | 1984-06-20 | ||
| DE3422809.8 | 1984-06-20 | ||
| DE3437665.8 | 1984-10-13 | ||
| DE3437665A DE3437665A1 (de) | 1984-06-20 | 1984-10-13 | Verfahren zur herstellung von 4-acylamino-2-alkylamino-phenylethern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6117549A JPS6117549A (ja) | 1986-01-25 |
| JPH0556334B2 true JPH0556334B2 (ja) | 1993-08-19 |
Family
ID=25822287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60132089A Granted JPS6117549A (ja) | 1984-06-20 | 1985-06-19 | ïŒâã¢ã·ã«ã¢ããâïŒâã¢ã«ãã«ã¢ããâããšãã«ãšãŒãã«ã®è£œæ³ |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0165564B1 (ja) |
| JP (1) | JPS6117549A (ja) |
| DE (2) | DE3437665A1 (ja) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3519983A1 (de) * | 1985-06-04 | 1986-12-04 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von 2,4-dinitrophenol-alkoxy-alkylethern |
| DE3519982A1 (de) * | 1985-06-04 | 1986-12-04 | Cassella Ag, 6000 Frankfurt | Verfahren zur herstellung von 2,4-dinitrophenylethern |
| JPS63157244U (ja) * | 1987-03-30 | 1988-10-14 | ||
| EP0285109B1 (de) * | 1987-04-02 | 1992-09-16 | Ciba-Geigy Ag | Verfahren zur Herstellung von 2-Amino-4-acylaminophenylethern |
| DE3804621A1 (de) * | 1988-02-13 | 1989-08-24 | Hoechst Ag | Verfahren zur herstellung von 4-acylamino-2-amino-alkoxybenzolen |
| FR2638453B1 (fr) * | 1988-10-28 | 1991-06-07 | Oreal | Ortho-aminophenols 5-substitues, procede pour les preparer et leur utilisation pour la teinture d'oxydation des fibres keratiniques |
| EP0415884A1 (de) * | 1989-08-28 | 1991-03-06 | Ciba-Geigy Ag | Verfahren zur Herstellung von aromatischen Aminen |
| JP5313703B2 (ja) * | 2009-01-16 | 2013-10-09 | å 山工æ¥æ ªåŒäŒç€Ÿ | ãšã³ã³ãŒãä»é§åäŒéçšãã«ãåã³ãã®è£œé æ¹æ³ã䞊ã³ã«ãå転æ€åºã·ã¹ãã |
| CN104557598A (zh) * | 2015-01-21 | 2015-04-29 | å®åŸœçæºåå·¥æéå ¬åž | 2-ç²æ°§åº-5-ä¹é °æ°šåºè¯èºçåæå·¥èº |
| CN114436876B (zh) * | 2020-10-30 | 2023-03-14 | äžåœç§åŠé¢å€§è¿ååŠç©çç 究æ | äžç§2-æ°šåº-4-ä¹é °æ°šåºè¯ç²éçè¿ç»åææ¹æ³ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0011048B1 (en) * | 1978-09-11 | 1982-01-27 | Toms River Chemical Corporation | A process for the manufacture of substantially pure 3-amino-4-alkoxy-acylanilides from 2,4-dinitrochlorobenzene |
| JPS5618945A (en) * | 1979-07-25 | 1981-02-23 | Sumitomo Chem Co Ltd | Preparation of 2,4-diaminophenyl ether |
| DE3222013A1 (de) * | 1982-06-11 | 1983-12-15 | Hoechst Ag, 6230 Frankfurt | Verfahren zur herstellung von kernsubstituierten n-alkylanilinen |
-
1984
- 1984-10-13 DE DE3437665A patent/DE3437665A1/de not_active Withdrawn
-
1985
- 1985-06-13 EP EP85107326A patent/EP0165564B1/de not_active Expired
- 1985-06-13 DE DE8585107326T patent/DE3562913D1/de not_active Expired
- 1985-06-19 JP JP60132089A patent/JPS6117549A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0165564A2 (de) | 1985-12-27 |
| EP0165564B1 (de) | 1988-05-25 |
| DE3437665A1 (de) | 1986-01-02 |
| EP0165564A3 (en) | 1987-01-14 |
| DE3562913D1 (en) | 1988-06-30 |
| JPS6117549A (ja) | 1986-01-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |