4-fluoro-2-hydroxybenzohydrazide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-fluorosalicylate (500 mg, 2.94 mmol, commercially available from e.g. Apollo, Alfa Aesar or ABCR) in methanol (15 ml) stirred under argon at room temp was added neat hydrazine monohydrate (0.722 ml, 14.69 mmol). The reaction mixture was stirred at 80° C. for 18 hr. The reaction mixture was concentrated in vacuo and partitioned between ethyl acetate (˜50 ml) and water (˜25 ml). The aqueous phase was extracted with ethyl acetate (2×25 ml) and the combined organic extracts washed with brine (25 ml), dried over sodium sulphate, evaporated in vacuo and dried (vacuum oven, 40° C., 24 hr) to afford the crude product as an off-white solid in 385 mg. The reaction mixture was concentrated in vacuo partitioned between ethyl acetate (˜50 ml) and water (˜25 ml) The aqueous phase was extracted with ethyl acetate (2×25 ml) the combined organic extracts washed with brine (25 ml) dried over sodium sulphate evaporated in vacuo dried (vacuum oven, 40° C., 24 hr)