tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate → HCID 10707324, compound
Reaction equation
[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([N:15]([CH2:23][CH3:24])C(=O)OC(C)(C)C)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.Cl>>[CH2:1]([O:8][C:9]1[C:10]([N+:25]([O-:27])=[O:26])=[C:11]([CH:12]=[CH:13][CH:14]=1)[NH:15][CH2:23][CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
3
Procedure
To tert-butyl N-(3-benzyloxy-2-nitrophenyl)-N-ethylcarbamate (3.30 g) was added 4N hydrogen chloride-ethyl acetate solution (15 ml) under ice-cooling, and the mixture was stirred for 10 minutes at the same temperature and then for 30 minutes at ambient temperature. The solvent was removed in vacuo, saturated sodium bicarbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo to give 3-benzyloxy-N-ethyl-2-nitroaniline (2.29 g).
Workup
- temperature