Hydrochloric Acid → 2-Benzyloxy-4-phenoxyphenylamine

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:22]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[In].Cl>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:11][C:10]=1[NH2:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Procedure

To a mixture of 2-benzyloxy-4-phenoxy-1-nitrobenzene (1.0 g, 3.12 mmol) and indium powder (1.0 g, 8.7 mmol) in THF (8 mL) is added concentrated HCl (1.5 mL) dropwise. The mixture is stirred at ambient temperature for 2.5 h. The solution is decanted from unreacted indium and 2N NaOH is added, which results in the formation of a gummy precipitate. The residue is triturated with EtOAc and centrifuged. The solution is decanted and the solvent removed under reduced pressure to afford a dark oil. The residue is purified by flash chromatography using DCM to elute 2-benzyloxy-4-phenoxyphenylamine as an oil: 1H NMR (CDCl3) δ 7.43-7.23 (m, 8H), 7.00 (t, 1H), 6.92-6.88 (m, 1H), 6.69 (d, J=8.33 Hz, 1H), 6.63 (d, J=2.52 Hz, 1H), 6.51 (dd, J=8.34, 2.52 Hz, 1H), 5.00 (s, 2H), 3.71 (br s, 2H); MS (M+H)+=292.