2-(4-Nitrophenyl)-4-methoxybenzothiophene → 2-(4-Aminophenyl)-4-methoxybenzothiophene

HRID 454803Notes

Reaction equation

HRID 454803 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:13]=3[CH:14]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:13]=3[CH:14]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 469469612-(4-Nitrophenyl)-4-methoxybenzothiopheneHCID 178418361HCID 178418361, compound

Product 1

HCID 469469662-(4-Aminophenyl)-4-methoxybenzothiophene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-(4-Nitrophenyl)-4-methoxybenzothiophene (1-1, 200 mg, 0.71 mmol) obtained in Example 1 and 10% palladium on charcoal (Pd/C, 5 mg) were added to a round bottom flask containing anhydrous methanol (10 mL) and sealed with a septum. Then, the flask is filled with hydrogen gas, provided with a hydrogen balloon and stirred at room temperature for 12 hours. Then, the resulting product was filtered using celite, and a methanol solvent was removed under reduced pressure to give the target compound 2-(4-aminophenyl)-4-methoxybenzothiophene (1-7, 151 mg, 88%).

Workup

  1. additionwere added to a round bottom flask
  2. customsealed with a septum

Sources & evidence

ORD record
ord-bfe4a517334f43a8bfff509100a664e6
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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