4-(4-Methoxypyridin-2-yl)-2-nitrotoluene → 5-(4-Methoxypyridin-2-yl)-2-methylaniline

HRID 1059975

Reaction equation

HRID 1059975 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([N+:16]([O-])=O)[CH:10]=2)[CH:4]=1>O1CCCC1.C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]([CH:10]=2)[NH2:16])[CH:4]=1

Participants

5

Reactant 1

HCID 186310034-(4-Methoxypyridin-2-yl)-2-nitrotoluene

Product 1

HCID 186676385-(4-Methoxypyridin-2-yl)-2-methylanilineYield 96.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 4-(4-methoxypyridin-2-yl)-2-nitrotoluene (300 mg) in tetrahydrofuran (3 ml) and ethanol (3 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 150 mg) under a hydrogen atmosphere for 3 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 5-(4-methoxypyridin-2-yl)-2-methylaniline (254 mg).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6ba881de2be0410e8f67d1743402cb68
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Linked notes

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