HCID 89814428, compound → 1-(3-Amino-4-fluorophenyl)butan-2-one

HRID 715086Notes

Reaction equation

HRID 715086 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:12])[CH2:10][CH3:11])=[CH:4][C:3]=1[N+:13]([O-])=O>CCOC(C)=O.[Pd]>[NH2:13][C:3]1[CH:4]=[C:5]([CH2:8][C:9](=[O:12])[CH2:10][CH3:11])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 89814428HCID 89814428, compound

Product 1

HCID 898141911-(3-Amino-4-fluorophenyl)butan-2-oneYield 75.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Treat a solution of 1-(4-fluoro-3-nitrophenyl)butan-2-one (0.83 g, 3.93 mmol) in EtOAc (30 mL) with 10% Pd/C (0.209 g, 0.197 mmol) and hydrogenate at atmospheric pressure (balloon) overnight. Remove the solids via filtration through diatomaceous earth, rinse well with EtOAc, concentrate the filtrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (536 mg, 75%). 1H NMR (400 MHz, DMSO-d6): δ 6.88 (dd, J=11.6, 8.2 Hz, 1H), 6.57 (dd, J=8.9, 2.1 Hz, 1H), 6.32 (m, 1H), 5.07 (s, 2H), 3.55 (s, 2H), 2.46 (q, J=7.3 Hz, 2H), 0.89 (t, J=7.3 Hz, 3H); MS (ESI) m/z: 182.1 (M+H+).

Workup

  1. customhydrogenate at atmospheric pressure (balloon) overnight
  2. customRemove the solids
  3. filtrationvia filtration through diatomaceous earth
  4. washrinse well with EtOAc
  5. concentrationconcentrate the filtrate to dryness
  6. custompurify via silica gel chromatography (EtOAc/Hex)

Sources & evidence

ORD record
ord-7e8500d0823940b5829de85096960f35
Source dataset
uspto-grants-2015_11
Patent number
US09187474B2

Reaction notes

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