1-Methoxy-4-(2-methyl-2-nitropropyl)benzene → 2-(4-Methoxyphenyl)-1,1-dimethylethylamine

HRID 2172708Notes

Reaction equation

HRID 2172708 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([CH3:15])([N+:12]([O-])=O)[CH3:11])=[CH:5][CH:4]=1>[Pd].CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([CH3:15])([NH2:12])[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 128269081-Methoxy-4-(2-methyl-2-nitropropyl)benzene

Product 1

HCID 918922-(4-Methoxyphenyl)-1,1-dimethylethylamineYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The crude 1-methoxy-4-(2-methyl-2-nitropropyl)benzene (200 mg, 0.96 mmol) was combined with palladium on carbon (40 mg) in methanol (30 mL). The suspension was vigorously stirred at room temperature under a hydrogen atmosphere overnight. The mixture was filtered through Celite and the filtrate was concentrated to give 1-(4-methoxyphenyl)-2-methylpropan-2-amine (150 mg, 88% yield) as a yellow oil which was used without further purification. (MS m/z: 180 (M+1)).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-25c2daae1d4d4fb896aeb45b4234735c
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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