HCID 59441773, compound → HCID 59441685, compound

HRID 1014388Notes

Reaction equation

HRID 1014388 reaction equation
[CH3:1][N:2]([C:9]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([O:18][CH3:19])=[CH:11][C:10]=1[CH3:20])[C:3](=[O:8])[CH2:4][N:5]([CH3:7])[CH3:6]>[Pd].CO>[NH2:15][C:13]1[C:12]([O:18][CH3:19])=[CH:11][C:10]([CH3:20])=[C:9]([N:2]([CH3:1])[C:3](=[O:8])[CH2:4][N:5]([CH3:7])[CH3:6])[CH:14]=1

Participants

4

Reactant 1

HCID 59441773HCID 59441773, compound

Product 1

HCID 59441685HCID 59441685, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

10% palladium on carbon (0.25 g, 8.52 mmol) was placed under N2 atm. MeOH (10 mL) was added, followed by a solution of N1,N2,N2-trimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide (1.86 g, 6.61 mmol) in MeOH (90 mL). The slurry was purged with N2, then was placed under H2 atm via a rubber balloon and maintained at rt for 2 days. The resulting mixture was filtered through Celite. The filtrate was concentrated. The oily residue was taken up into Et2O and concentrated again to obtain N1-[5-amino-2-methyl-4-(methyloxy)phenyl]-N1,N2,N2-trimethylglycinamide as a white foamy solid (1.41 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.00 (s, 3H), 2.11 (s, 6H), 2.58 (d, J=15.57 Hz, 1H), 2.77 (d J=15.57 Hz, 1H), 2.97 (s, 3H), 3.77 (s, 3H), 4.70 (s, 2H), 6.41 (s, 1H), 6.72 (s, 1H); ESIMS (M+H)+=252.10.

Workup

  1. customThe slurry was purged with N2
  2. filtrationThe resulting mixture was filtered through Celite
  3. concentrationThe filtrate was concentrated
  4. concentrationconcentrated again

Sources & evidence

ORD record
ord-3eba24fcd50f4aa1aa8c5ac287f69a55
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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