Water → HCID 15125647, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 10.9 g (54 mmol) of methyl 4-amino-5-chlorosalicylate hydrochloride diluted with 250 ml pyridine is stirred at 0° C. and treated with 17 g (0.22 mol, 16 mls) of acetyl chloride over a 10 minute period. A ppt. begins to form and the mixture is stirred 30 minutes longer at 0° C. This is then treated with 30 ml H2O and stirred for 5 minutes after which time the ppt. dissolves. The mixture is diluted with CH2Cl2 (500 ml), washed with H2O (500 ml) and 10% HCl (4×300 ml). The organic layer is dried (MgSO4) and evaporated to dryness to obtain crude product which is recrystallyzed from ethylacetate-hexane to obtain pure methyl 2-acetoxy-4-acetylamino-5-chlorobenzoate; m.p. 134°-36° C.

Provenance & Evidence