Benzaldehyde → HCID 3772128, compound

Participants

Reaction Steps

To a solution of N-methylanilinoborane dichloride (100 mg) in methylene chloride (5 ml), a solution of benzaldehyde (56 mg) and tri-n-butylamine (99 mg) in methylene chloride (2 ml) is added with ice cooling, and the resultant mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with methylene chloride. The methylene chloride layer is washed with aqueous sodium carbonate and a saturated brine in that order, and evaporated under reduced pressure to remove the solvent. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylaminobenzhydrol (85 mg) as crystals melting at 124° to 126° C. The yield is 75.0%.

Provenance & Evidence