Hydroxyamine hydrochloride → 2-(Hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid
Reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([CH2:12][C:13](=S)[C:14]([OH:16])=[O:15])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:19][OH:20]>[O-]CC.[Na+]>[OH:20][N:19]=[C:13]([CH2:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:8]=1)[C:14]([OH:16])=[O:15]Participants
4
Procedure
3-(4-Phenylthiophen-2-yl)-2-thioxopropanoic acid (0.9 g, 3.4 mmol), hydroxylamine hydrochloride (740 mg, 10.6 mmol), and an ethanolic solution sodium ethoxide [prepared from 0.4 g of sodium and 30 mL of absolute ethanol] was refluxed for 1.5 h. Solvent was removed under reduced pressure and the residue was diluted with water and acidified with 1.5N HCl to adjust the pH of the solution ˜3. The solid product was extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, then removal of the solvent under reduced pressure yielded 2-(hydroxyimino)-3-(4-phenylthiophen-2-yl)propanoic acid (0.8 g, yield 89%) as an off-white solid. 1H NMR (400 MHz, MeOD) δ 7.59-7.57 (m, 2H), 7.37-7.33 (m, 3H), 7.24-7.23 (m, 2H), 3.31 (s, 2H). MS (ESI) m/z: Calculated for C13H11NO3S: 262.05. found: 262.0 (M+H)+.