Diisopropylamine → HCID 178506292, compound

Participants

Reaction Steps

Normal-butyllithium (a 2.6 M solution in hexane, 87.2 mL) was dropwise added to a solution of N,N-diisopropylamine (25.0 g) in tetrahydrofuran (hereinafter referred to as THF, 300 mL) under a nitrogen atmosphere at −5 to 0° C., and a solution of 2-fluoropyridine (25 g) in THF (50 mL) was dropwise added thereto at −78° C., followed by stirring for 1 hr. Subsequently, a solution of ethyl trifluoroacetate (47.6 g) in THF (50 mL) was dropwise added to the reaction solution at −78° C., followed by stirring at the same temperature for 1 hr. Hydrazine monohydrate (41.3 g) was added thereto, followed by stirring at 60° C. for 6 hr. Water (500 mL) was added to the reaction solution, followed by stirring at 100° C. for 30 min. The precipitate was collected by filtration and dried under reduced pressure to obtain a compound (1a) (32.8 g, 85%) as a white solid.

Provenance & Evidence