Sodium Hydroxide → HCID 86008531, compound

Participants

Reaction Steps

A mixture of 2-chloro-3-methylpyridine-4-carbaldehyde (58.35 g, 375 mmol) and cyclopropylamine (52.6 mL, 750 mmol) in MeOH (800 mL) was stirred overnight at rt. The mixture was cooled to 0° C. and NaBH4 (18.4 g, 488 mmol) was added portionwise. The mixture was stirred overnight at rt. Aq. 1M NaOH (250 mL) was added and the solvents were partially removed under reduced pressure. The aq. phase was extracted with EtOAc (3×). The combined org. phases were washed with brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification fy FC yielded the compound (54.56 g, 74%) as a pale yellow liquid.

Provenance & Evidence