Hydroxyamine hydrochloride → HCID 86659950, compound

Reaction equation

[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1.Cl.[NH2:15][OH:16].C(=O)(O)[O-].[Na+]>CO>[OH:16][N:15]=[C:6]([NH2:7])[C:5]1[CH:8]=[CH:9][C:2]([CH3:1])=[CH:3][C:4]=1[C:10]([F:13])([F:11])[F:12]

Participants

Procedure

An oven-dried 20 mL reaction vial containing a stir bar was cooled under a stream of dry nitrogen. The vial was charged with 4-methyl-2-(trifluoromethyl)benzonitrile (1000 mg, 5.40 mmol), hydroxylamine hydrochloride (469 mg, 6.75 mmol), sodium bicarbonate (681 mg, 8.10 mmol), and methanol (6 mL). The vial was flushed with nitrogen, sealed, stirred at room temperature for 30 minutes, and then placed in a sand bath set to 75° C. and stirred overnight. The crude reaction material was purified by reverse phase preparative HPLC. The collected product fractions were evaporated under vacuum to afford N′-hydroxy-4-methyl-2-(trifluoromethyl)benzimidamide (0.54 g, 2.45 mmol, 45% yield). MS M+1=219.0.