4-Fluorophenylhydrazine hydrochloride → HCID 67206078, compound

HRID 2366564Notes

Reaction equation

HRID 2366564 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

5

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 14615292Benzyl (4-oxocyclohexyl)carbamate

Product 1

HCID 67206078HCID 67206078, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. temperatureat reflux for 1 h30
  2. washwashed with sat.aq
  3. extractionThe aqueous phase was extracted twice with EA
  4. washthe combined organic extracts were washed with sat. aq. NaHCO3 solution, water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa82c7a8886f4e02b6a2f53043e82dfd
Source dataset
uspto-grants-2014_04
Patent number
US08697869B2

Reaction notes

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