HCID 53833682, compound → 4-(3,4-Dimethoxyphenethyl)aniline

HRID 488487Notes

Reaction equation

HRID 488487 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)=[CH:5][C:4]=1[O:20][CH3:21]>CN(C)C=O.[Pd]>[CH3:21][O:20][C:4]1[CH:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 53833682HCID 53833682, compound

Product 1

HCID 142560244-(3,4-Dimethoxyphenethyl)anilineYield 63%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

1,2-Dimethoxy-4-[2-(4-nitrophenyl)ethenyl]benzene (12.1 g, 0.042 mol) was reduced in the presence of 10% Pd—C (2.0 g) in dimethylformamide (DMF) (120 mL) at 25° C. under a hydrogen atmosphere. The reaction mixture was concentrated in vacuo to give a solid. The solid was recrystallized from MeOH (400 mL) to yield a white crystalline product, 6.8 g (0.026 mol, 63%) of the desired product. mp 115-116° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a solid
  3. customThe solid was recrystallized from MeOH (400 mL)

Sources & evidence

ORD record
ord-d18d6e50016b484a9bbf9276693b91ef
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

Loading…