3-Ethynyl-4-fluoroaniline → 3-Ethyl-4-fluoroaniline

HRID 2367143Notes

Reaction equation

HRID 2367143 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:6])#[CH:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][C:9]=1[F:10])[NH2:6])[CH3:2]

Participants

5

Reactant 2

HCID 126873623-Ethynyl-4-fluoroanilineHCID 178418361HCID 178418361, compound

Product 1

HCID 207143403-Ethyl-4-fluoroanilineYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-ethynyl-4-fluoroaniline (220 mg, 1.62 mmol) in ethyl acetate (10 mL) was added 10% palladium on carbon (wet). The resulting mixture was subjected to an atmosphere of hydrogen for approximately 1 h. The palladium on carbon was removed by filtration through celite. The filtrate was concentrated in vacuo to provide 3-ethyl-4-fluoroaniline (154 mg, 1.11 mmol, 69% yield) as a brown oil. 1H NMR (400 MHz, CDCl3): 6.77 (dd, 1H), 6.50 (dd, 1H), 6.45-6.41 (m, 1H), 3.47 (br s, 2H), 2.57 (q, 2H), 1.19 (t, 3H); MS (EI) for C8H10FN: 140 (MH+).

Workup

  1. customThe palladium on carbon was removed by filtration through celite
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e5a90b582d0c4e78b4524725ab08feb3
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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