Methyl 5-chloropyrazine-2-carboxylate → 5-Chloropyrazinoic acid

Temperature

160 °C

To a solution of methyl-5-chloropyrazine-2-carboxylate (120 mg, 0.70 mmol) in a mixture of acetonitrile (2 mL) and DMF (1 mL) was added lithium chloride (295 mg, 6.95 mmol). The suspension was heated to 160° C. for 5 mins in a Smith creator microwave after which time the reaction was diluted with water (10 mL). Saturated sodium bicarbonate solution (20 mL) was added and the aqueous layered extracted twice with ethyl acetate (30 mL). The combined organics were discarded and the aqueous layer adjusted to pH 4 with 1N hydrochloric acid. The aqueous phase was extracted twice with ethyl acetate (20 mL) and the combined organics washed with water (2×20 mL), brine (10 mL) and dried (MgSO4). The volatiles were removed to give the title compound as a colourless solid (68 mg).

1. extractionthe aqueous layered extracted twice with ethyl acetate (30 mL)
2. extractionThe aqueous phase was extracted twice with ethyl acetate (20 mL)
3. washthe combined organics washed with water (2×20 mL), brine (10 mL)
4. dry with materialdried (MgSO4)
5. customThe volatiles were removed

ORD record

ord-29b76f63099c409ea5a7e8bb3755f4cd

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977328B2