N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide → N2-(2-Amino-4,6-dimethylphenyl)-N1,N1-dimethylglycinamide

HRID 656834Notes

Reaction equation

HRID 656834 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([N+:9]([O-])=O)[C:3]=1[NH:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]>CCO.[Pd]>[NH2:9][C:4]1[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([CH3:1])[C:3]=1[NH:12][CH2:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 68995353N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide

Product 1

HCID 68997231N2-(2-Amino-4,6-dimethylphenyl)-N1,N1-dimethylglycinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N2-(2,4-dimethyl-6-nitrophenyl)-N1,N1-dimethylglycinamide from Step A (2.54 g, 10.1 mmol) in EtOH (50 mL) was added 10% Pd/C (500 mg). The reaction mixture was stirred under a hydrogen atmosphere (ca. 1 atm) for 72 h, then filtered through a Celite pad, washing with EtOH, and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc —100:0 to 0:100, to give the title compound. MS: m/z=222 (M+1).

Workup

  1. filtrationfiltered through a Celite pad
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with a gradient of hexane:EtOAc —100:0 to 0:100

Sources & evidence

ORD record
ord-4f7514d485bd4bbcb78458638ac06865
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

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