4-Fluorophenylhydrazine hydrochloride → HCID 59161212, compound

HRID 545500Notes

Reaction equation

HRID 545500 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.O=[C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]1>Cl>[F:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:14][C:13]2=1

Participants

4

Reactant 2

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamide

Product 1

HCID 59161212HCID 59161212, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Combine p-fluorophenylhydrazine hydrochloride (5.00 g, 30.7 mmol) and N-(4-oxo-cyclohexyl)isobutyramide (5.64 g, 30.7 mmol) in ethanolic HCl (125 mL) and heat at reflux under nitrogen for 18 h. Concentrate the reaction in vacuo to remove most of the EtOH, dilute with water and extract with EtOAc. Wash the EtOAc extracts with water and brine, dry over Na2SO4, and evaporate to give 7.1 g (56%) of a beige solid. MS (ES): m/z 275 (M+1); 1H NMR(DMSO-d6): δ 10.79 (s, 1H, NH), 7.81 (d, 1H, J=7.5 Hz), 7.19 (dd, 1H, J=8.6, 4.6 Hz), 7.07 (d, 1H, J=10.1 Hz), 6.79 (dt, 1H, J=8.9, 1.8 Hz), 4.00 (m, 1H), 2.85 (dd, 1H, J=15.0, 5.3 Hz), 2.76 (m, 2H), 2.39 (m, 2H), 1.93 (m, 1H), 1.75 (m, 1H), 0.99 (d, 6H, J=6.6 Hz).

Workup

  1. temperatureat reflux under nitrogen for 18 h
  2. concentrationConcentrate
  3. customthe reaction in vacuo
  4. customto remove most of the EtOH
  5. additiondilute with water
  6. extractionextract with EtOAc
  7. washWash the EtOAc
  8. dry with materialdry over Na2SO4
  9. customevaporate

Sources & evidence

ORD record
ord-b0ff8d24e73042a5ba5bd6ac7d073c25
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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