3-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide → 4-amino-3-methoxy-N-(1-methylpyrrolidin-3-yl)benzamide

HRID 2234457Notes

Reaction equation

HRID 2234457 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[N+:18]([O-])=O)[C:6]([NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10]1)=[O:7]>CO.[Pd]>[NH2:18][C:17]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][CH:9]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10]2)=[O:7])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 686830363-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide2×

Product 1

HCID 686841234-amino-3-methoxy-N-(1-methylpyrrolidin-3-yl)benzamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-methoxy-N-[(3R)-1-methylpyrrolidin-3-yl]-4-nitro-benzamide (Intermediate 188; 227 mg, 0.81 mmol) in methanol (25 mL) was hydrogenated using 10% Pd/C catalyst. Catalyst was filtered off and solvent evaporated to yield the title compound as a yellow gum (200 mg, 100%).

Workup

  1. filtrationCatalyst was filtered off
  2. customsolvent evaporated

Sources & evidence

ORD record
ord-683e4ef4c211450a9676a7f0eac795d8
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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