2-Isopropyl-1-methoxy-4-nitrobenzene → 4-Methoxy-3-(propan-2-yl)aniline

HRID 502630Notes

Reaction equation

HRID 502630 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[O:13][CH3:14])([CH3:3])[CH3:2]>CO.[Pd]>[CH:1]([C:4]1[CH:9]=[C:8]([CH:7]=[CH:6][C:5]=1[O:13][CH3:14])[NH2:10])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 148281912-Isopropyl-1-methoxy-4-nitrobenzene

Product 1

HCID 148281924-Methoxy-3-(propan-2-yl)anilineYield 108.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Isopropyl-1-methoxy-4-nitro-benzene (4.53 g, 23.6 mmol) was dissolved in 100 mL of methanol in presence of 0.4 g of 10% Pd/C in a Parr bottle, and then subjected to 40 psi of H2 overnight at room temperature. The mixture was purged with nitrogen for 10 minutes and filtered over Celite. The filtrate was concentrated to give 4.22 g 3-isopropyl-4-methoxyaniline.

Workup

  1. customsubjected to 40 psi of H2 overnight at room temperature
  2. customThe mixture was purged with nitrogen for 10 minutes
  3. filtrationfiltered over Celite
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1d6bb59e00a149bd8120450f152546b0
Source dataset
uspto-grants-2010_08
Patent number
US07776872B2

Reaction notes

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