Diisobutylaluminum hydride → 2-(3-Chloro-phenyl)-propane-1,2-diamine

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Reaction Steps

A solution of compound 2-amino-2-(3-chloro-phenyl)-propionitrile (8.0 g) in toluene (60 mL) was cooled to −78° C. and DIBAL-H solution (132 mL of a 1M solution in toluene) was added to it drop wise under nitrogen. The reaction mixture was slowly warmed to room temperature and then left at stirring for 17 h. Reaction was monitored by TLC. After completion, the reaction mixture was quenched with 30 mL methanol and then 100 mL water. All solvents were evaporated and the crude mass was taken in 50 mL water and acidified to pH=1 with 1M HCl. Organic impurities were extracted with ethyl acetate and the aqueous layer was basified to pH=14 with 30% NaOH solution. The free diamine, 2-(3-chloro-phenyl)-propane-1,2-diamine, was extracted with dichloromethane, dried over sodium sulfate, filtered and concentrated (4.2 g). The material was used crude in the next reaction step. MS (ESI): 185.1 (MH+).

Provenance & Evidence