2-(cyclopropylamino)-N-methyl-3-nitrobenzamide → 3-amino-2-(cyclopropylamino)-N-methylbenzamide

HRID 2036573Notes

Reaction equation

HRID 2036573 reaction equation
[CH:1]1([NH:4][C:5]2[C:14]([N+:15]([O-])=O)=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]([NH:9][CH3:10])=[O:8])[CH2:3][CH2:2]1>CO.[Pd]>[NH2:15][C:14]1[C:5]([NH:4][CH:1]2[CH2:3][CH2:2]2)=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([NH:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 584592352-(cyclopropylamino)-N-methyl-3-nitrobenzamide

Product 1

HCID 584592993-amino-2-(cyclopropylamino)-N-methylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(cyclopropylamino)-N-methyl-3-nitrobenzamide (1.76 g, 7.48 mmol) in MeOH (25 mL) was added palladium 10 wt % on carbon (180 mg, 75 mmol) under N2. After flushing the flask with N2 for 2 min, the solution was stirred under a H2 balloon for 3 h. LC-MS showed the reaction was complete. The reaction mixture was filtered and the filtrates collected, rinsed with MeOH and concentrated. The residue was purified by column chromatography on a silica gel column using EtOAc:DCM (1:1) as eluent to give 3-amino-2-(cyclopropylamino)-N-methylbenzamide: 1H NMR (400 MHz, CDCl3) δ 6.85-6.80 (m, 3H), 6.20 (br, 1H), 5.94 (br, 1H), 4.07 (br, 1H), 2.98 (d, J=4 Hz, 3H), 2.63-2.55 (m, 1H), 0.65-0.53 (m, 4H); LCMS (ESI) m/z 206.1 [M+H]+.

Workup

  1. customAfter flushing the flask with N2 for 2 min
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrates collected
  4. washrinsed with MeOH
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on a silica gel column

Sources & evidence

ORD record
ord-2b75e0d4d8f24b20875985759de6c073
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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