Ethylenediamine → 3-(1,1-Difluoroethyl)aniline

HRID 1898313Notes

Reaction equation

HRID 1898313 reaction equation
[F:1][C:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([F:4])[CH3:3].C(N)CN>CO.[Pd]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])([F:4])[CH3:3]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 108778561-(1,1-Difluoroethyl)-3-nitrobenzene

Product 1

HCID 234450923-(1,1-Difluoroethyl)anilineYield 95.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(1,1-difluoroethyl)-3-nitrobenzene (1.00 g, 5.34 mmol) in methanol (5.0 mL) was added Pd/C (catalytic amount) and ethylene diamine (catalytic amount). The reaction mixture was subjected for hydrogenation in Parr apparatus under 30 psi for 5-6 h. The excess of solvent was removed under vacuum to afford 0.800 g of the desired product. 1HNMR (DMSO-d6): δ 1.88 (d, J=18.0 Hz, 3H), 3.74 (s, 1H), 7.72 (t, J=8.4 Hz, 1H), 6.81 (s, 1H), 6.87 (d, J=7.8 Hz, 1H), 7.19 (t, J=7.8 Hz, 1H).

Workup

  1. customThe excess of solvent was removed under vacuum

Sources & evidence

ORD record
ord-333024e0e2f84a2b99a92e0d4718169b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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