5-BROMO-N-(CARBOXYMETHYL)ANTHRANILIC ACID synthesis
- Product Name:5-BROMO-N-(CARBOXYMETHYL)ANTHRANILIC ACID
- CAS Number:32253-75-1
- Molecular formula:C9H8BrNO4
- Molecular Weight:274.07
Yield:32253-75-1 60%
Reaction Conditions:
Stage #1: chloroacetic acid;5-Bromo-2-aminobenzoic acidwith sodium carbonate in water at 80;
Stage #2: with hydrogenchloride in diethyl ether;water;
Steps:
1.1.6
(6) 2-(N-carboxymethylamino)-5-bromobenzoic acid To a solution of 2-amino-5-bromobenzoic acid (2 g, 9 mmol) in 15 ml of 2 N Na2CO3, a solution of chloroacetic acid (0.69 g, 7.3 mmol) in 7.5 ml of 2 N Na2CO3 was slowly added dropwise. Then, after stirred for 20 hours at 80 °C, the reaction mixture was cooled down to room temperature. 50 ml of ether and 8 ml of 2 N hydrochloric acid were added to the mixture. The organic phase was separated, and dried with MgSO4. After evaporation, a light brown solid was obtained. The solid was purified by silica gel column chromatography (ethyl acetate/methanol, v/v, 1/1) to obtain a white solid (2-(N-carboxymethylamino)-5-bromobenzoic acid) (1.55 g, yield: 60%; mp: 178-180 °C).
References:
EP2168964,2010,A1 Location in patent:Page/Page column 13
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32253-75-1
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