CH380743A - Verfahren zur Herstellung von Halogenaminobenzoesäuren oder deren funktionellen Derivaten - Google Patents
Verfahren zur Herstellung von Halogenaminobenzoesäuren oder deren funktionellen DerivatenInfo
- Publication number
- CH380743A CH380743A CH6965559A CH6965559A CH380743A CH 380743 A CH380743 A CH 380743A CH 6965559 A CH6965559 A CH 6965559A CH 6965559 A CH6965559 A CH 6965559A CH 380743 A CH380743 A CH 380743A
- Authority
- CH
- Switzerland
- Prior art keywords
- acids
- functional derivatives
- nickel
- haloaminobenzoic
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 239000002253 acid Substances 0.000 title description 5
- 150000007513 acids Chemical class 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 13
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 238000006722 reduction reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052759 nickel Inorganic materials 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- -1 hydroxylamino compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JAHIPDTWWVYVRV-UHFFFAOYSA-N 4-chloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O JAHIPDTWWVYVRV-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- MPOQCWWYSFKEET-UHFFFAOYSA-N 2-chloro-N-[2-(diethylamino)ethyl]-4-nitrobenzamide hydrochloride Chemical compound Cl.CCN(CC)CCNC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl MPOQCWWYSFKEET-UHFFFAOYSA-N 0.000 description 1
- QAYNSPOKTRVZRC-UHFFFAOYSA-N 99-60-5 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl QAYNSPOKTRVZRC-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000005415 aminobenzoic acids Chemical class 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229960002038 chloroprocaine hydrochloride Drugs 0.000 description 1
- SZKQYDBPUCZLRX-UHFFFAOYSA-N chloroprocaine hydrochloride Chemical compound Cl.CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl SZKQYDBPUCZLRX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- TYFRHNVPASRWLT-UHFFFAOYSA-N ethyl 2-bromo-4-nitrobenzoate Chemical compound CCOC(=O)C1=CC=C([N+]([O-])=O)C=C1Br TYFRHNVPASRWLT-UHFFFAOYSA-N 0.000 description 1
- NAHVMSGNHQCHBM-UHFFFAOYSA-N ethyl 4-amino-2-bromobenzoate Chemical compound CCOC(=O)C1=CC=C(N)C=C1Br NAHVMSGNHQCHBM-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- PICNSXCJRMYANX-UHFFFAOYSA-N methyl 2-chloro-4-nitrobenzoate Chemical compound COC(=O)C1=CC=C([N+]([O-])=O)C=C1Cl PICNSXCJRMYANX-UHFFFAOYSA-N 0.000 description 1
- DSHBGNPOIBSIOQ-UHFFFAOYSA-N methyl 4-amino-2-chlorobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1Cl DSHBGNPOIBSIOQ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT288958A AT206888B (de) | 1958-04-21 | 1958-04-21 | Verfahren zur Herstellung von Halogen-aminobenzoesäuren und deren Derivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH380743A true CH380743A (de) | 1964-08-15 |
Family
ID=3541903
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6965559A CH380743A (de) | 1958-04-21 | 1959-02-17 | Verfahren zur Herstellung von Halogenaminobenzoesäuren oder deren funktionellen Derivaten |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT206888B (enrdf_load_stackoverflow) |
| BE (1) | BE576810A (enrdf_load_stackoverflow) |
| CH (1) | CH380743A (enrdf_load_stackoverflow) |
| FR (1) | FR1219962A (enrdf_load_stackoverflow) |
| GB (1) | GB903404A (enrdf_load_stackoverflow) |
| NL (1) | NL237001A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3530181A (en) * | 1965-02-03 | 1970-09-22 | Shell Oil Co | Herbicidal benzamides |
-
0
- BE BE576810D patent/BE576810A/xx unknown
- NL NL237001D patent/NL237001A/xx unknown
-
1958
- 1958-04-21 AT AT288958A patent/AT206888B/de active
-
1959
- 1959-02-17 CH CH6965559A patent/CH380743A/de unknown
- 1959-04-03 GB GB1139459A patent/GB903404A/en not_active Expired
- 1959-04-15 FR FR792151A patent/FR1219962A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB903404A (en) | 1962-08-15 |
| BE576810A (enrdf_load_stackoverflow) | |
| FR1219962A (fr) | 1960-05-20 |
| NL237001A (enrdf_load_stackoverflow) | |
| AT206888B (de) | 1959-12-28 |
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