HCID 21914168, compound → HCID 21914167, compound

HRID 730940Notes

Reaction equation

HRID 730940 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[CH:10][C:9]=2[O:17][CH3:18])[CH:5]=[CH:6][CH:7]=1.[H][H]>O1CCCC1.CO.[Pt](=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[C:12]([CH:11]=[CH:10][C:9]=2[O:17][CH3:18])[NH2:14])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 21914168HCID 21914168, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21914167HCID 21914167, compoundYield 89.5%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(3-chlorophenyl)-4-nitroanisole (0.5 g, 1.9 mmol) in tetrahydrofuran (5 mL) and methanol (5 mL) was added platinum (IV) oxide (1 mg). The reaction was stirred at room temperature under one atmosphere of hydrogen for 4.5 hours. The slurry was filtered through Celite and concentrated under reduced pressure to afford 3-(3-chlorophenyl)-4-methoxyaniline as a light yellow oil (405 mg, 1.7 mmol).

Workup

  1. filtrationThe slurry was filtered through Celite
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f60fd9706e5048bb9558d27b78e0c90c
Source dataset
uspto-grants-2009_09
Patent number
US07582765B2

Reaction notes

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