N-(2,6-dimethyl-3-nitrophenyl)acetamide → N-(3-amino-2,6-dimethylphenyl)acetamide

HRID 579970

Reaction equation

HRID 579970 reaction equation
[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([N+:12]([O-])=O)[C:6]=1[CH3:15])(=[O:3])[CH3:2].[H][H]>CO.C(O)C.C(O)(=O)C.[C].[Pd]>[C:1]([NH:4][C:5]1[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]([NH2:12])[C:6]=1[CH3:15])(=[O:3])[CH3:2]

Participants

7

Reactant 2

HCID 223591N-(2,6-dimethyl-3-nitrophenyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 847848N-(3-amino-2,6-dimethylphenyl)acetamide

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

N-Acetyl-2,6-dimethyl-3-nitroaniline (30.6 g; 0.15 mole) was dissolved in a mixture of methanol (100 ml), ethanol (50 ml) and acetic acid (100 ml). To the resulting solution was added 2.0 g of 10% palladium carbon and the mixture was stirred in a stream of hydrogen at room temperature for 26 hours. The catalyst was filtered off, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from ethanol-ether to give 22.0 g (84%) of the title object compound as crystals, m.p. 195°-197° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe residue was recrystallized from ethanol-ether
  4. customto give 22.0 g (84%) of the title

Sources & evidence

ORD record
ord-2fb60170b6424a21bf9371ac5f963b87
Source dataset
uspto-grants-1988_06
Patent number
US04751232

Linked notes

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