Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].[OH:9][CH2:10][C:11]1[NH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][C:16]([C:20]#[N:21])=[CH:15][CH:14]=2>CCO>[OH:3][NH:2][C:20]([C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH2:10][OH:9])=[CH:19]2)=[NH:21]Hydroxylamine hydrochloride (243 mg) and sodium bicarbonate (586 mg) was added to a solution of 2-(hydroxymethyl)-1H-indole-5-carbonitrile (D24) (300 mg) in EtOH (20 mL), in that sequence. The reaction mixture was heated to 50° C. and stirred for 24 hours at that temperature. Another portion of hydroxylamine hydrochloride (100 mg) was added, followed by addition of sodium bicarbonate (220 mg). The resulting suspension was stirred at 50° C. for 7 hours. The inorganics was filtered off. The filtrate was concentrated to afford a pale yellow oil. Trituration of the residue provided N-hydroxy-2-(hydroxymethyl)-1H-indole-5-carboximidamide (D25) (300 mg) as a pale yellow solid. MS (ES): C10H11N3O2 requires 205; found 206.2 (M+H+).
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