N2,N2-dimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide → N1-[5-amino-2-methyl-4-(methyloxy)phenyl]-N2,N2-dimethylglycinamide
Reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([N+:13]([O-])=O)[C:10]([O:16][CH3:17])=[CH:9][C:8]=1[CH3:18])=[O:5]>CO.[Pd]>[NH2:13][C:11]1[C:10]([O:16][CH3:17])=[CH:9][C:8]([CH3:18])=[C:7]([NH:6][C:4](=[O:5])[CH2:3][N:2]([CH3:19])[CH3:1])[CH:12]=1Participants
Procedure
N2,N2-dimethyl-N1-[2-methyl-4-(methyloxy)-5-nitrophenyl]glycinamide (0.642 mg, 2.4 mmol) was suspended in methanol (20 ml) and Pd/C (65 mg) was added. The reaction vessel was subjected to H2 at 60 psi on a Fisher Porter apparatus. After stirring overnight, the reaction was not complete so more Pd (from a new bottle) was added and the vessel resubjected to H2 at 60 psi on a Fisher Porter apparatus for an additional 18 h. Pd/C was removed from the reaction by filtering through a pad of celite and washing with MeOH. Solvents were removed under reduced pressure and the residue was purified by SiO2 chromatography to afford N1-[5-amino-2-methyl-4-(methyloxy)phenyl]-N2,N2-dimethylglycinamide (435 mg, 1.83 mmol) as a orange solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.05 (s, 3 H) 2.30 (s, 6 H) 3.00 (s, 2 H) 3.72 (s, 3 H) 4.54 (s, 2 H) 6.62 (s, 1 H) 6.90 (s, 1 H) 8.97 (s, 1 H).
Workup
- additionwas added
- waitthe vessel resubjected to H2 at 60 psi on a Fisher Porter apparatus for an additional 18 h
- customPd/C was removed from the reaction
- filtrationby filtering through a pad of celite
- washwashing with MeOH
- customSolvents were removed under reduced pressure
- customthe residue was purified by SiO2 chromatography
Sources & evidence
- ORD record
- ord-a8f50355ac194830914b12c6c52edec8
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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