3-Methoxy-5-nitro-biphenyl → 5-Methoxy-[1,1'-biphenyl]-3-amine

HRID 1063084Notes

Reaction equation

HRID 1063084 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([NH2:9])[CH:6]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 222833303-Methoxy-5-nitro-biphenyl

Product 1

HCID 222831725-Methoxy-[1,1'-biphenyl]-3-amineYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Methoxy-5-nitro-biphenyl (176 mg, 0.77 mmol) are hydrogenated in ethanol (5 ml) using palladium on carbon (10%, 17 mg) at atmospheric pressure for 2 h. The catalyst is filtered off and the solvent removed in vacuo. Flash chromatography (silica, eluent ethyl acetate/cyclohexane 1:1) affords the product (139 mg, 91%) as a bown oil. MS: m/e=199 (M+).

Workup

  1. customfor 2 h
  2. filtrationThe catalyst is filtered off
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ba5db2f8f8f44995bc15372cb104b52b
Source dataset
uspto-grants-2005_11
Patent number
US06963000B2

Reaction notes

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