Hydrazine hydrate (1:1) → HCID 55280958, compound

Temperature

80 °C

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.

1. concentrationThe reaction mixture was concentrated in vacuo
2. custompartitioned between ethyl acetate (˜50 ml) and water (˜25 ml)
3. extractionThe aqueous phase was extracted with ethyl acetate (2×25 ml)
4. washthe combined organic extracts washed with brine (25 ml)
5. dry with materialdried over sodium sulphate
6. customevaporated in vacuo
7. customdried (vacuum oven, 40° C., 24 hr)

ORD record

ord-a1f0567e95484d4fbd36428b7522d1c7

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501946B2