Hydrochloric Acid → [(4-Methoxyphenyl)(nitroso)amino]acetic acid

Reaction equation

[N:1]([O-:3])=O.[Na+].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1.Cl>O>[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]([N:1]=[O:3])[CH2:14][C:15]([OH:17])=[O:16])=[CH:11][CH:12]=1

Participants

Procedure

Sodium nitrite (3.97 g, 57.5 mmol) in 10 mL of water was added to a suspension of N-(4-methoxyphenyl)glycine (9.92 g, 54.7 mmol) in 50 mL of water under N2. This was allowed to stir at room temperature until solution clarified, about 6 hours. The solution was acidified with concentrated hydrochloric acid to pH 3 and a precipitate formed. The solid was collected and washed with 50 mL water, then dried in vacuo to give 11.50 g (100%) of the desired compound as a white solid. 1H NMR (CDCl3): δ7.17 (d, J=8.8, 2H); 6.70 (d, J=8.8, 2H); 4.30 (s, 2H), 3.56 (s, 3H), 2.29 (br s, 1H).