N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide → N-(5-amino-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide

HRID 384262Notes

Reaction equation

HRID 384262 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([O:14][CH2:15][CH2:16][N:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:9]=1

Participants

4

Reactant 1

HCID 58098809N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide

Product 1

HCID 58098633N-(5-amino-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamideYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(5-nitro-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide (430 mg) in EtOH (10 mL) was added Pd/C (200 mg) and was charged with H2 (1 atm). After stirring for 3 h, Pd/C was removed by filtration and the filtrate was concentrated to give N-(5-amino-2-(2-(pyrrolidin-1-yl)ethoxy)phenyl)acetamide (380 mg).

Workup

  1. additionwas charged with H2 (1 atm)
  2. customPd/C was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d1633ed141fa4999a8ebff19c862db2f
Source dataset
uspto-grants-2013_02
Patent number
US08367689B2

Reaction notes

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