Acetic Acid → 4-(4-amino-2-fluorophenyl)-N,N-dimethylbutanamide

HRID 1192872Notes

Reaction equation

HRID 1192872 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15].C(O)(=O)C>C(OCC)(=O)C.[Fe]>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:11][CH2:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])=[C:2]([F:1])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 687351604-(2-fluoro-4-nitrophenyl)-N,N-dimethylbutanamide

Product 1

HCID 687334484-(4-amino-2-fluorophenyl)-N,N-dimethylbutanamideYield 89.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
21 °C

Procedure

A solution of compound 4-(2-Fluoro-4-nitrophenyl)-N,N-dimethylbutanamide (77) (15 mg, 0.06 mmol), Fe (20 mg, 0.37 mmol) and acetic acid (1 mL) in ethyl acetate (3 mL) was heated under reflux for 2 h. The reaction mixture was allowed to cool to 21° C. and then filtered. The organic layer was concentrated and the residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1) to give desired 4-(4-Amino-2-fluorophenyl)-N,N-dimethylbutanamide (76) (12 mg, 87%): 1H NMR δ 6.95 (dd, 1H, J=8.3, 8.2 Hz), 6.40 (dd, 1H, J=8.3, 2.2 Hz), 6.35 (dd, 1H, J=11.6, 2.2 Hz), 3.66 (br s, 2H), 2.95 (s, 3H), 2.93 (s, 3H), 2.58 (t, 2H, J=7.4 Hz) 2.30 (t, 2H, J=7.6 Hz) 1.85-1.95 (m, 2H).

Workup

  1. temperatureunder reflux for 2 h
  2. filtrationfiltered
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified with silica gel column chromatography (dichloromethane:acetone, 9:1)

Sources & evidence

ORD record
ord-e6af859bb99d454c8e9c7698ab49bbeb
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

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