Pyridine → Methyl 3-(4-(2-acetylhydrazinecarbonyl)phenoxy)-5-(benzyloxy)benzoate

Participants

Reaction Steps

To a stirring solution of 4-[3-(benzyloxy)-5-(methoxycarbonyl)phenoxy]benzoic acid (Intermediate 11) (34 g, 82.87 mmol, 1 equiv) in dry DCM (50 mL), DMF (1.5 mL, catalytic) was added followed by oxalyl chloride (20.1 g, 158.7 mmol, 2 equiv.) dropwise at 0-5° C. The reaction mixture was stirred at room temperature for 2 h. After 2 h, a mixture of acetic hydrazide (8.8 g, 119 mmol, 1.5 equiv.) and dry pyridine (12.4 mL, 158.7 mmol, 2 equiv.) in dry DCM (50 mL) was added to the above prepared acid chloride at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 min. The reaction was monitored by TLC. After completion, the reaction mixture was diluted with dil. HCl and extracted with DCM. The organic layer was washed with water, brine and dried over sodium sulphate and concentrated to afford white solid. (32 g).

Provenance & Evidence