3-methyl-N-(1-methylethyl)-2-nitrobenzeneacetamide → 2-amino-3-methyl-N-(1-methylethyl)benzeneacetamide

HRID 905518Notes

Reaction equation

HRID 905518 reaction equation
[CH3:1][C:2]1[C:3]([N+:15]([O-])=O)=[C:4]([CH2:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH:5]=[CH:6][CH:7]=1>[Pd].C(O)C>[NH2:15][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:8][C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10]

Participants

4

Reactant 1

HCID 673911893-methyl-N-(1-methylethyl)-2-nitrobenzeneacetamide2×

Product 1

HCID 673906992-amino-3-methyl-N-(1-methylethyl)benzeneacetamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 3-methyl-N-(1-methylethyl)-2-nitrobenzeneacetamide (i.e. the title product of Step A) (0.40 g, 1.7 mmol) and 10% palladium on carbon (0.13 g) was added 20 mL of ethanol. The reaction mixture was placed under a balloon of nitrogen overnight. Then the reaction mixture was filtered through Celite® diatomaceous filter aid. The solvent was removed with a rotary evaporator to afford the title compound as a tan solid (0.29 g).

Workup

  1. customwas placed under a balloon of nitrogen overnight
  2. filtrationThen the reaction mixture was filtered through Celite® diatomaceous filter aid
  3. customThe solvent was removed with a rotary evaporator

Sources & evidence

ORD record
ord-724fa7862a134c53b681cc5d9fd722e1
Source dataset
uspto-grants-2011_09
Patent number
US08012499B2

Reaction notes

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