DE1543885C3 - Verfahren zur Herstellung von 2-Methoxy^-amino-S-chlorbenzoesäuremethylester - Google Patents
Verfahren zur Herstellung von 2-Methoxy^-amino-S-chlorbenzoesäuremethylesterInfo
- Publication number
- DE1543885C3 DE1543885C3 DE1543885A DE1543885A DE1543885C3 DE 1543885 C3 DE1543885 C3 DE 1543885C3 DE 1543885 A DE1543885 A DE 1543885A DE 1543885 A DE1543885 A DE 1543885A DE 1543885 C3 DE1543885 C3 DE 1543885C3
- Authority
- DE
- Germany
- Prior art keywords
- amino
- methoxy
- preparation
- methyl ester
- acid methyl
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- YDPNBRVAZXOPLH-UHFFFAOYSA-N 4-amino-5-chloro-2-hydroxybenzoic acid Chemical compound NC1=CC(O)=C(C(O)=O)C=C1Cl YDPNBRVAZXOPLH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 3
- -1 methyl halide Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- ALYQFGBPEGLBLW-UHFFFAOYSA-N methyl 4-amino-5-chloro-2-methoxybenzoate Chemical compound COC(=O)C1=CC(Cl)=C(N)C=C1OC ALYQFGBPEGLBLW-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- FWUALUHYKLDYAN-UHFFFAOYSA-N 3-amino-4-chlorophenol Chemical compound NC1=CC(O)=CC=C1Cl FWUALUHYKLDYAN-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000003474 anti-emetic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C205/60—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms in ortho-position to the carboxyl group, e.g. nitro-salicylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Footwear And Its Accessory, Manufacturing Method And Apparatuses (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7613165 | 1965-12-10 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1543885A1 DE1543885A1 (de) | 1970-01-02 |
| DE1543885B2 DE1543885B2 (de) | 1973-08-02 |
| DE1543885C3 true DE1543885C3 (de) | 1974-02-28 |
Family
ID=13596371
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1543885A Expired DE1543885C3 (de) | 1965-12-10 | 1966-12-02 | Verfahren zur Herstellung von 2-Methoxy^-amino-S-chlorbenzoesäuremethylester |
Country Status (12)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102311357B (zh) * | 2011-10-17 | 2014-01-08 | 上海安诺芳胺化学品有限公司 | 2-羟基-4-氨基苯甲酸的制备方法 |
-
1966
- 1966-11-25 IL IL26947A patent/IL26947A/en unknown
- 1966-11-30 FI FI663184A patent/FI48066C/fi active
- 1966-11-30 BE BE690476D patent/BE690476A/xx not_active IP Right Cessation
- 1966-12-02 DE DE1543885A patent/DE1543885C3/de not_active Expired
- 1966-12-06 ES ES0334733A patent/ES334733A1/es not_active Expired
- 1966-12-07 CS CS7793A patent/CS150934B2/cs unknown
- 1966-12-08 FR FR86769A patent/FR1504227A/fr not_active Expired
- 1966-12-08 NO NO165905A patent/NO132956C/no unknown
- 1966-12-09 CH CH1762266A patent/CH486415A/fr not_active IP Right Cessation
- 1966-12-09 BR BR185258/66A patent/BR6685258D0/pt unknown
- 1966-12-10 OA OA52690A patent/OA02685A/xx unknown
- 1966-12-12 GB GB55530/66A patent/GB1159938A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES334733A1 (es) | 1967-10-16 |
| DE1543885A1 (de) | 1970-01-02 |
| NO132956C (enrdf_load_stackoverflow) | 1976-02-11 |
| CS150934B2 (enrdf_load_stackoverflow) | 1973-09-17 |
| OA02685A (fr) | 1970-12-15 |
| CH486415A (fr) | 1970-02-28 |
| BE690476A (enrdf_load_stackoverflow) | 1967-05-30 |
| FI48066C (fi) | 1974-06-10 |
| FR1504227A (fr) | 1967-12-01 |
| DE1543885B2 (de) | 1973-08-02 |
| BR6685258D0 (pt) | 1973-12-04 |
| GB1159938A (en) | 1969-07-30 |
| NO132956B (enrdf_load_stackoverflow) | 1975-11-03 |
| IL26947A (en) | 1970-12-24 |
| FI48066B (enrdf_load_stackoverflow) | 1974-02-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |