ChemicalBook CAS DataBase List 4-CHLORO-N,2-DIHYDROXYBENZAMIDE

4-CHLORO-N,2-DIHYDROXYBENZAMIDE synthesis

3synthesis methods

Product Name:4-CHLORO-N,2-DIHYDROXYBENZAMIDE
CAS Number:61799-78-8
Molecular formula:C7H6ClNO3
Molecular Weight:187.58

22717-55-1 Synthesis

22717-55-1
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61799-78-8
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Yield:61799-78-8 88%

Reaction Conditions:

Stage #1: methyl 4-chloro-2-hydroxybenzoatewith hydroxylamine hydrochloride;sodium hydroxide in ethanol;water at 20; for 24 h;Cooling with ice;Inert atmosphere;
Stage #2: with hydrogenchloride for 0.5 h;Reflux;

Steps:

1.2

2) Preparation of 4-chloro-N,2-dihydroxy-benzamide Hydroxylamine hydrochloride in solid (5.25g, 75 mmol) is placed in an egg type flask and dissolved by drop-adding small amount of water in ice-bath. Thereafter, thereto is drop-added 15 ml of 50% NaOH solution. The reaction is stirred for 5 minutes and is drop-added 50 ml of dioxane solution of methyl 4-chloro-salicylate (9.3g, 50 mmol) under coverage of N₂. After completion of drop-addition, a reaction is carried out at room temperature for 24 hours, and then a red-brown deposit precipitates, which is filtered out and placed in an egg type flask, thereto is added 50 ml of 10% hydrochloric acid and then reflux for 0.5 hour. After cooling to room temperature, a yellow deposit precipitates, which is filtered out and recrystallized in anhydrous ethanol, to obtain 8.25g of 4-chloro-N,2-dihydroxy-benzamide, with a yield of 88%.

References:

EP2322520,2011,A1 Location in patent:Page/Page column 12