HCID 59441965, compound → N-(3-Amino-4-methylphenyl)-N~2~,N~2~-dimethylglycinamide

HRID 1014224Notes

Reaction equation

HRID 1014224 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[C:9]([N+:14]([O-])=O)[CH:8]=1)=[O:5]>C(OCC)(=O)C.[Pd]>[NH2:14][C:9]1[CH:8]=[C:7]([NH:6][C:4](=[O:5])[CH2:3][N:2]([CH3:17])[CH3:1])[CH:12]=[CH:11][C:10]=1[CH3:13]

Participants

4

Reactant 1

HCID 59441965HCID 59441965, compound

Product 1

HCID 17607975N-(3-Amino-4-methylphenyl)-N~2~,N~2~-dimethylglycinamideYield 148.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N2,N2-dimethyl-N1-(4-methyl-3-nitrophenyl)glycinamide (7.0 g, 19.5 mmol) was dissolved in ethyl acetate and 10% Pd/C (500 mg) was added. The reaction was placed on a Fischer-Porter hydrogenation apparatus and treated with 50 psi of H2 gas overnight. Following purging with N2 the reaction solution was passed through a celite plug to afford analytically pure N1-(3-amino-4-methylphenyl)-N2,N2-dimethylglycinamide (6.0 g, 29.0 mmol, 98% yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.96 (s, 3 H), 2.24 (s, 6 H), 2.97 (s, 2 H), 4.79 (s, 2 H), 6.63 (dd, J=8.05, 2.01 Hz, 1 H), 6.78 (d, J=8.05 Hz, 1 H), 6.96 (d, J=2.01 Hz, 1 H), 9.24 (s, 1 H).

Workup

  1. additiontreated with 50 psi of H2 gas overnight
  2. customFollowing purging with N2 the reaction solution

Sources & evidence

ORD record
ord-0c889ef6bc47487caf823ab3081bcbcc
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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