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Benzoic acid, 3-amino-5-chloro-4-hydroxy-, methyl ester synthesis
- Product Name:Benzoic acid, 3-amino-5-chloro-4-hydroxy-, methyl ester
- CAS Number:40258-68-2
- Molecular formula:C8H8ClNO3
- Molecular Weight:201.61
![Methyl 3-chloro-4-hydroxy-5-nitrobenzoate](/CAS/20200331/GIF/40256-81-3.gif)
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![Benzoic acid, 3-amino-5-chloro-4-hydroxy-, methyl ester](/CAS/20200401/GIF/40258-68-2.gif)
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Yield:40258-68-2 68%
Reaction Conditions:
with iron;ammonium chloride in methanol;water; for 16.1667 h;Heating / reflux;
Steps:
50.1
Step 1. A solution of 3-chloro-4-hydroxy-5-nitro-benzoic acid methyl ester (500 mg, 2.16 mmol) in methanol (22 mL) was added within 10 min to a mixture of iron powder (410 mg, 7.34 mmol) ammonium chloride (647 mg, 12.1 mmol) in water (22 mL). The reaction mixture was heated at reflux over 16 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was extracted with ethyl acetate, dried (MgSO4), and evaporated. Chromatography (SiO2, ethyl acetate/heptane 7:3) afforded 3-amino-5-chloro-4-hydroxy-benzoic acid methyl ester (293 mg, 68%). Light yellow solid, MS (ISP)=200.1 (M-H)-.
References:
US2007/191603,2007,A1 Location in patent:Page/Page column 35-36
![METHYL 3-CHLORO-4-HYDROXYBENZOATE](/CAS/GIF/3964-57-6.gif)
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![Benzoic acid, 3-amino-5-chloro-4-hydroxy-, methyl ester](/CAS/20200401/GIF/40258-68-2.gif)
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