HCID 68686226, compound → HCID 58674311, compound

HRID 1994121Notes

Reaction equation

HRID 1994121 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([N+:17]([O-])=O)[CH:8]=1>CCOC(C)=O.[Pd]>[NH2:17][C:9]1[CH:8]=[C:7]([CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=1)[C:6]([NH:5][CH2:4][CH2:3][O:2][CH3:1])=[O:20]

Participants

4

Reactant 1

HCID 68686226HCID 68686226, compound

Product 1

HCID 58674311HCID 58674311, compoundYield 924%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a stirred solution of N-(2-methoxyethyl)-3-nitro-5-(trifluoromethyl)benzamide (760 mg, 0.26 mmol) in EtOAc (20 mL) was added Pd on carbon (10% wt, 76 mg). The mixture was allowed to stir at rt overnight under an atmosphere of hydrogen. The mixture was diluted with EtOAc and filtered through Celite. The filtrate was evaporated and the residue was purified by column chromatography (SiO2, MeOH/DCM) to yield the title compound as a white solid (630 mg, 92%). LCMS: (FA) ES+ 263.2 (M+1)

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. customthe residue was purified by column chromatography (SiO2, MeOH/DCM)

Sources & evidence

ORD record
ord-e456c73acaba45268435b901899c5525
Source dataset
uspto-grants-2010_01
Patent number
US07652041B2

Reaction notes

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