DE2316459C2 - Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamiden - Google Patents
Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamidenInfo
- Publication number
- DE2316459C2 DE2316459C2 DE2316459A DE2316459A DE2316459C2 DE 2316459 C2 DE2316459 C2 DE 2316459C2 DE 2316459 A DE2316459 A DE 2316459A DE 2316459 A DE2316459 A DE 2316459A DE 2316459 C2 DE2316459 C2 DE 2316459C2
- Authority
- DE
- Germany
- Prior art keywords
- nitrobenzene
- carboxylic acid
- carboxamides
- alkyl ester
- acid alkyl
- 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 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 alkyl 1-nitrobenzene Chemical compound 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 150000001733 carboxylic acid esters Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2316459A DE2316459C2 (de) | 1973-04-03 | 1973-04-03 | Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamiden |
| US455375A US3892797A (en) | 1973-04-03 | 1974-03-27 | Process for the preparation of 1-nitroben zene-2-carboxylic acid alkyl ester-5-carboxylic acid amides |
| CH460374A CH590209A5 (show.php) | 1973-04-03 | 1974-04-02 | |
| FR7411651A FR2224451B1 (show.php) | 1973-04-03 | 1974-04-02 | |
| JP3668874A JPS5735703B2 (show.php) | 1973-04-03 | 1974-04-02 | |
| GB1449074A GB1408552A (en) | 1973-04-03 | 1974-04-02 | Process for the manufacture of 1-nitrobenzene-2-carboxylic acid alkyl ester-5-carboxylic acid amides |
| BE142800A BE813242A (fr) | 1973-04-03 | 1974-04-03 | Procede de preparation de 1-nitro-2-alcoxy-carbonyl-5-carbamoyl-benzenes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2316459A DE2316459C2 (de) | 1973-04-03 | 1973-04-03 | Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamiden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2316459A1 DE2316459A1 (de) | 1974-10-24 |
| DE2316459C2 true DE2316459C2 (de) | 1982-06-24 |
Family
ID=5876794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2316459A Expired DE2316459C2 (de) | 1973-04-03 | 1973-04-03 | Verfahren zur Herstellung von 1- Nitrobenzol-2-carbonsäure-alkylester-5-carbonsäureamiden |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3892797A (show.php) |
| JP (1) | JPS5735703B2 (show.php) |
| BE (1) | BE813242A (show.php) |
| CH (1) | CH590209A5 (show.php) |
| DE (1) | DE2316459C2 (show.php) |
| FR (1) | FR2224451B1 (show.php) |
| GB (1) | GB1408552A (show.php) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2497797A1 (fr) * | 1981-01-13 | 1982-07-16 | Synthelabo | Procede de preparation de l'amino-4 butyramide |
| US4551549A (en) * | 1981-08-17 | 1985-11-05 | E. I. Du Pont De Nemours And Company | Preparation and use of nitroterephthalamic acids |
| JPH07581U (ja) * | 1993-05-31 | 1995-01-06 | 株式会社遠藤製作所 | 浴槽用浄水器 |
| CN111592465A (zh) * | 2019-02-20 | 2020-08-28 | 武汉珈汇精化科技有限公司 | 一种制备2-氨基-4-氨甲基苯甲酸甲酯及其盐酸盐的方法 |
-
1973
- 1973-04-03 DE DE2316459A patent/DE2316459C2/de not_active Expired
-
1974
- 1974-03-27 US US455375A patent/US3892797A/en not_active Expired - Lifetime
- 1974-04-02 GB GB1449074A patent/GB1408552A/en not_active Expired
- 1974-04-02 JP JP3668874A patent/JPS5735703B2/ja not_active Expired
- 1974-04-02 CH CH460374A patent/CH590209A5/xx not_active IP Right Cessation
- 1974-04-02 FR FR7411651A patent/FR2224451B1/fr not_active Expired
- 1974-04-03 BE BE142800A patent/BE813242A/xx not_active IP Right Cessation
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2316459A1 (de) | 1974-10-24 |
| FR2224451A1 (show.php) | 1974-10-31 |
| CH590209A5 (show.php) | 1977-07-29 |
| JPS5735703B2 (show.php) | 1982-07-30 |
| JPS49127940A (show.php) | 1974-12-07 |
| BE813242A (fr) | 1974-10-03 |
| GB1408552A (en) | 1975-10-01 |
| FR2224451B1 (show.php) | 1978-03-24 |
| US3892797A (en) | 1975-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8339 | Ceased/non-payment of the annual fee |