1-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine → 4-((Dimethylamino)methyl)-2-methoxyaniline

HRID 2205919Notes

Reaction equation

HRID 2205919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][N:13]([CH3:15])[CH3:14])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CCO.[Pd]>[CH3:15][N:13]([CH2:12][C:5]1[CH:6]=[CH:7][C:8]([NH2:9])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:14]

Participants

4

Reactant 1

HCID 220464651-(3-Methoxy-4-nitrophenyl)-N,N-dimethylmethanamine

Product 1

HCID 220462864-((Dimethylamino)methyl)-2-methoxyanilineYield 98.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd on carbon (12 mg, 0.866 mmol) was added to a solution of 1-(3-methoxy-4-nitrophenyl)-N,N-dimethylmethanamine (Preparation 109, 160 mg, 0.76 mmol) in EtOH (3 mL). The reaction mixture was degassed and then stirred for 1 hour at room temperature under an atmosphere of hydrogen before being filtered on a pad of Celite and concentrated under reduced pressure to afford the title compound (0.135 g, 98%).

Workup

  1. customThe reaction mixture was degassed
  2. filtrationbefore being filtered on a pad of Celite
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-517c8583a8f54bccb7f8733f5f1abf39
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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