Triethylsilane → 2-(3-Aminophenyl)-N,N-dimethylacetamide

HRID 1487118Notes

Reaction equation

HRID 1487118 reaction equation
[CH3:1][N:2]([CH3:15])[C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1.C([SiH](CC)CC)C>CO.[Pd]>[NH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([N:2]([CH3:1])[CH3:15])=[O:14])[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 85858599HCID 85858599, compound

Product 1

HCID 286896572-(3-Aminophenyl)-N,N-dimethylacetamideYield 88.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of N,N-dimethyl-2-(3-nitrophenyl)acetamide (1.6 g, 7.68 mmol) in methanol (20 ml) was added 10% Pd—C (0.327 g,) followed by slow addition of triethylsilane (12.3 ml, 77 mmol) at RT. Reaction was stirred at same temperature for 30 min. The reaction mixture was filtered through celite bed. The filtrate was concentrated to get 2-(3-aminophenyl)-N,N-dimethylacetamide (1.21 g, 88% yield).

Workup

  1. customReaction
  2. filtrationThe reaction mixture was filtered through celite bed
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e62fc4bbe0ec422fb03242f1ceba0d8b
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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