Ethyl 2-chlorobenzyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate → Ethyl 2-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamate

HRID 495619Notes

Reaction equation

HRID 495619 reaction equation
[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([N+:21]([O-])=O)=[CH:13][C:12]=1[N+:24]([O-])=O)[C:6](=[O:10])[O:7][CH2:8][CH3:9]>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:30]=[CH:29][CH:28]=[CH:27][C:3]=1[CH2:4][N:5]([C:11]1[C:16]([C:17]([F:20])([F:19])[F:18])=[CH:15][C:14]([NH2:21])=[CH:13][C:12]=1[NH2:24])[C:6](=[O:10])[O:7][CH2:8][CH3:9]

Participants

4

Reactant 1

HCID 20827734Ethyl 2-chlorobenzyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate

Product 1

HCID 20827733Ethyl 2-chlorobenzyl[2,4-diamino-6-(trifluoromethyl)phenyl]carbamateYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-chlorobenzyl[2,4-dinitro-6-(trifluoromethyl)phenyl]carbamate (103.8 mg) was dissolved in ethyl acetate (20 ml), and to the solution was added 10% Pd—C (105.3 mg). The reaction mixture was stirred under hydrogen atmosphere for 7 hours. The catalyst was filtered, and washed with ethyl acetate. The filtrate was concentrated in vacuo to give the title compound (85.6 mg).

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-42b2cb5cb8b84dfab453a2c3b421b67a
Source dataset
uspto-grants-2005_09
Patent number
US06939887B2

Reaction notes

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