2-Amino-N-methyl-3-nitrobenzamide → HCID 21877363, compound

HRID 1861111Notes

Reaction equation

HRID 1861111 reaction equation
[NH2:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]>CCOC(C)=O.[Pd]>[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]

Participants

4

Reactant 1

HCID 123249782-Amino-N-methyl-3-nitrobenzamide

Product 1

HCID 21877363HCID 21877363, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-N-methyl-3-nitro-benzamide (1.4 g, 7.2 mmol) was reduced by hydrogenation using 50 psi of H2 with 10% Pd—C (250 mg) in EtOAc (25 mL) for 5 h. After filtering through Celite, solvent was removed in vacuo. Purification by silica gel chromatography (10% MeOH/CHCl3) gave 1.08 mg (91%) of 2,3-diamino-N-methyl-benzamide as a faintly yellow solid. 1H NMR (300 MHz, CDCl3) δ 6.87 (dd, 1H, J=7.8, 1.5 Hz), 6.76 (dd, 1H, J=7.8, 1.5 Hz), 6.59 (t, 1H, J=7.8 Hz), 6.14 (br s, 1H), 4.28 (br s, 4H), 2.95 (d, 3H, J=5.1 Hz).

Workup

  1. customfor 5 h
  2. filtrationAfter filtering through Celite, solvent
  3. customwas removed in vacuo
  4. customPurification by silica gel chromatography (10% MeOH/CHCl3)

Sources & evidence

ORD record
ord-3d1b599d13dd49f6b33de4adf33561c0
Source dataset
uspto-grants-2003_03
Patent number
US06531491B1

Reaction notes

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