3-Isopropoxy-4-nitrotoluene → 4-Methyl-2-(propan-2-yloxy)aniline

HRID 1110431Notes

Reaction equation

HRID 1110431 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:7]=1.[H][H]>CO.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:12])=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 2

HCID 5927313-Isopropoxy-4-nitrotolueneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 150681144-Methyl-2-(propan-2-yloxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Methyl-1-(1-methylethoxy)-2-nitrobenzene, 17.7 g (91 mmol), is dissolved in methanol, palladium on charcoal is added and the mixture is exposed to hydrogen gas until the required amount of hydrogen is absorbed. The mixture is worked up in the usual manner to give 15 g of 4-methyl-2-(1-methylethoxy)benzenamine.

Workup

  1. customis absorbed

Sources & evidence

ORD record
ord-7e4950a4355741209f6cd1b0394f8712
Source dataset
uspto-grants-1990_12
Patent number
US04975456

Reaction notes

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