IE47799B1 - 5-substituted 2-methoxy-4-aminobenzoic acids and their preparation - Google Patents
5-substituted 2-methoxy-4-aminobenzoic acids and their preparationInfo
- Publication number
- IE47799B1 IE47799B1 IE2020/81A IE202081A IE47799B1 IE 47799 B1 IE47799 B1 IE 47799B1 IE 2020/81 A IE2020/81 A IE 2020/81A IE 202081 A IE202081 A IE 202081A IE 47799 B1 IE47799 B1 IE 47799B1
- Authority
- IE
- Ireland
- Prior art keywords
- methoxy
- amino
- acid
- benzoic acid
- substituted
- Prior art date
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
This invention provides 2-methoxy-4-aminohenzoic acids of the formula :
in which Q- is R^S- or R2S°2_ and E2 is a ethyl, propyl or isopropyl radical.
In accordance with the present invention, the new compounds are prepared by treating 2-methoxy-4-amino-5-mercaptohenzoic acid with a suitable alkyl sulphate to give the corresponding compound in which Q- is R^S-, l-e- 3 2-methoxy-4-amino-?-alkylthioben30ic acid,
ID followed if desired by oxidizing the latter with hydrogen peroxide to give the corresponding compound in which Q is R^SOg-, i.e. a 2~mcthoxy-4-amino-5-alkylsulphonylbcnzoic acid. These compounds are useful as intermediate compounds in syntheses of pharmacologically valuable :o.-anisamides, which are claimed in Patent Snecification
, No. 92/79.
A7799
- 3 The following Examples illustrate but do not limit the invention.
EXAMPLE 1
2-methoxv-4-amino-5-ethvIthiohenzoic acid
150 g °f 2-methoxy-4-amino-5-mercaptobenzoic acid, 555 cc of water and 160 cc of caustic soda solution are placed in a flask fitted with a condenser. The mixture is heated until the solid dissolves, then 123 g of ethyl sulphate is added. The mixture is heated to reflux, treated with 10 cc of 30% caustic soda solution and then heated to reflux for 1 hour. After cooling, 800 cc of water is added and the solution is filtered. The precipitate obtained hy adding 100 cc of concentrated hydrochloric acid in the presence of ether is drained, washed with water and dried.
162 g of 2-methoxy-4-amino-5-ethyltbio-benzoic acid is obtained (yield = 88%).
EXAMPLE 2
2-methoxy-4-amino-5-ethylsulphonyl-benzoic acid
123 g of 2-methoxy-4_amino-5-ethylthiobenzoic acid is dissolved hot in 542 cc of acetic acid. The solution obtained is cooled to 35*C, then 185 cc of 131 vol. hydrogen peroxide is added in small quantities while the temperature is raised to 80’C,
The temperature is lowered to 40°C and the mixture is kept at that temperature for some hours and then cooled to 10°C.
The precipitate formed is drained, washed with acetic acid, dried, and then dissolved in 600 cc of water and 100 cc of 20% ammonia.
The precipitate formed by adding 70 cc of concentrated hydrochloric acid is cooled, drained, washed with water and dried.
61.5 g of 2-methoxy-4-amino-5-ethylsulphonyl-benzoic acid hydrate is obtained (yield 42% - M.P. 95~1θθ’θ).
EXAMPLE 5
2-rneth3xy-4-aTtlno-5-propylthic>-beri2olc acid.
Following the same procedure as in Example 1 and starting with 2-racthoxy-4— amino-5-mercapto benzoic acid and propyl sulphate, 2-methoxy~4—amino-5—propvlthio-benzoic acid is obtained (M.P. =
104 - 105'C).
EXAMPLE 4
2-methoxy-4-amino-5-propylsulphonyl-benzoic acid
Following the same procedure as in Example 2, 137 g of 2-methoxy-4-amino-5-propylthio-benzoic acid dissolved in 570 ml of acetic acid is treated with 233 ml of HO vol. hydrogen peroxide.
108 g of 2-methoxy-4-amino-5-propylsulphonyl benzoic acid 10 is obtained (yield = 6950 - M.P. = 165 - l66°C).
EXAMPLE 5
2-methoxy-4—amino-5-methylthio-benzoic acid
Following the same procedure as in Example 1 and starting with 2-methoxy-4-amino-5-mercaptohenzoic acid and methyl sulphate,
2-methoxy-4-amino-5-methylthio-benzoic acid is obtained (M.P. =
151 - 152eC).
EXAMPLE 6
2-methoxy-4-amino-5-methylsulphonyl-benzoic acid
Following the same procedure as in Example 2, 158 g of
2-methoxy-4-amino-5-methylthio-benzoic acid dissolved in 7^2 ml of acetic acid is treated with 310 ml of 110 vol. hydrogen, peroxide.
114.5 g of 2-methoxy-4-amino-5-methylsulphoayl-henzoic acid is obtained (yield = 6>% - M.P. = 178 - 180°C).
Claims (6)
1. , 2-Methoxy-4-amino-5-alkylthiobenzoic acids of the formula : where Bg is a methyl, ethyl, propyl or isopropyl radical.
2. 2-Methory-4-amino-5-alkylsulphonyl-benzoic acids of the where Eg is as defined in Claim 1.
3. A method of preparing a compound as claimed in Claim 1 10 comprising treating 2-raethoxy-4-amino-5-mercaptobenzoic acid with a methyl, ethyl, propyl or isopropyl sulphate. 4. -7799
4. A method of preparing a compound as claimed in Claim 2 comprising oxidizing the corresponding compound of Claim 1 with hydrogen peroxide.
5. A method as claimed in Claim 3 substantially as hereinbefore described in Example 1, 3 or 5.
6. A method as claimed in Claim 4 substantially as hereinbefore described in Example 2, 4 or 6.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7801632A FR2415099A1 (en) | 1978-01-20 | 1978-01-20 | NEW DERIVATIVES OF 4-AMINO-5-ALKYLSULFONYL ORTHO-ANISAMIDES, THEIR METHODS OF PREPARATION AND THEIR APPLICATION AS PSYCHOTROPES |
| FR7801633A FR2424909A1 (en) | 1978-01-20 | 1978-01-20 | N-Cycloalkyl-pyrrolidino-benzamide derivs. - with central nervous system activity |
| IE92/79A IE47798B1 (en) | 1978-01-20 | 1979-01-30 | Substituted ortho-anisamides,methods of preparing them,compositions containing them and their application as psychotropic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE812020L IE812020L (en) | 1979-07-20 |
| IE47799B1 true IE47799B1 (en) | 1984-06-27 |
Family
ID=27250799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2020/81A IE47799B1 (en) | 1978-01-20 | 1979-01-30 | 5-substituted 2-methoxy-4-aminobenzoic acids and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| IE (1) | IE47799B1 (en) |
-
1979
- 1979-01-30 IE IE2020/81A patent/IE47799B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE812020L (en) | 1979-07-20 |
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