N-(2-(dimethylamino)ethyl)-3-methoxy-4-nitrobenzamide → 4-amino-N-(2-(dimethylamino)ethyl)-3-methoxybenzamide

HRID 1503849Notes

Reaction equation

HRID 1503849 reaction equation
[CH3:1][N:2]([CH3:19])[CH2:3][CH2:4][NH:5][C:6](=[O:18])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-])=O)=[C:9]([O:16][CH3:17])[CH:8]=1>CO.[Pd]>[NH2:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:19])=[O:18])=[CH:8][C:9]=1[O:16][CH3:17]

Participants

4

Reactant 1

HCID 68683674N-(2-(dimethylamino)ethyl)-3-methoxy-4-nitrobenzamide

Product 1

HCID 580150424-amino-N-(2-(dimethylamino)ethyl)-3-methoxybenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a suspension of the product of Example 31A (5.4 g, 20.2 mmol) in methanol (200 mL) was added 10% palladium on carbon (540 mg) and the mixture was stirred under hydrogen for 4 hours. The catalyst was filtered off and the filtrate was concentrated to give the title compound. MS: 238 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-13c5866269c840dbb9b3571e5ed8a9fc
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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