Hydrochloric Acid → HCID 87490606, compound

Participants

Reaction Steps

To a solution of 2-fluoro-5-methylaminobenzonitrile (307 mg, 2.04 mmol) in dry diethyl ether (10 ml) stirred at room temperature under nitrogen, was added dropwise by syringe diisobutylaluminium hydride (2.8 ml, 1.0 M in toluene, 2.8 mmol, 1.4 eq) and stirring continued for 19.5 h. The solution was chilled in an ice-bath and methanol (1.0 ml) was added dropwise and the mixture stirred for 1 h before 1.0 M HCl (9 ml) was added and stirring continued for a further 1 h. The reaction mixture was basified with NaOH (0.4 g) then partitioned between ether (50 ml) and water (50 ml) and the aqueous layer re-extracted with ether (50 ml). The combined ether extract was washed with brine (50 ml), dried over MgSO4 and evaporated to give an orange oil (289 mg), which was subjected to column chromatography (silica gel, 30×190 mm) eluting with 100% dichloromethane, affording 2-fluoro-5-methylaminobenzaldehyde (viii) as a yellow crystalline solid (162 mg, 52%), mp 36-38° C.

Provenance & Evidence