Sodium Hydroxide → 4-Methoxy-3-methyl-2-[(5-methyl-pyridine-2-carbonyl)-amino]-benzoic acid methyl ester

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Reaction Steps

2-Amino-4-methoxy-3-methyl-benzoic acid methyl ester (400 mg, 2 mmol) and 5-methyl-pyridine-2-carboxylic acid (280 mmol, 2 mmol) where dissolved in dichloro-methane (8 ml) and pyridine (1 ml). Phosphorous oxychloride (0.37 ml) was added while cooling on ice-bath. The mixture was left at 0° C. for 1 h then allowed to attain room temperature. Aqueous sodium hydroxide (20 ml, 1M) was added and the mixture were extracted with dichloromethane. Purification by column chromatography on silica gel (ether-pentane 1:1) gave pure title compound (410 mg, 65%). MS (M−H)+ 315.1

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