4-Fluorophenylhydrazine hydrochloride → HCID 67206078, compound

Reaction equation

O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][CH2:3]1.Cl.[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27]N)=[CH:23][CH:22]=1>CC(O)=O.CC(=O)OCC>[F:20][C:21]1[CH:22]=[C:23]2[C:24](=[CH:25][CH:26]=1)[NH:27][C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:4][C:3]2=1

Participants

Procedure

A solution of benzyl (4-oxocyclohexyl)carbamate (21.7 g, 87.8 mmol) and 4-fluorophenylhydrazine hydrochloride (14.3 g, 87.8 mmol) in glacial AcOH (148 ml) was stirred at reflux for 1 h30. After cooling to rt, the reaction mixture was diluted with EA and washed with sat.aq. NaHCO3 solution. The aqueous phase was extracted twice with EA, the combined organic extracts were washed with sat. aq. NaHCO3 solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo to give the title compound as a light brown foam which was used for the next step without further purification.