Methanol → 4,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine

HRID 32220Notes

Reaction equation

HRID 32220 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([N+:11]([O-])=O)=[C:5]([C:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH:15]=2)[CH:4]=1.CO>[Pd].O1CCCC1>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][C:6]([NH2:11])=[C:5]([CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)[CH:4]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 231419224,5-Dimethoxy-1-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene

Product 1

HCID 231418854,5-Dimethoxy-2-(3,3,5,5-tetramethylcyclohexyl)phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,5-dimethoxy-1-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene (1.0 g, 3.13 mmol) produced in Example (87b), 10% palladium on carbon (500 mg, wet), methanol (8 mL) and tetrahydrofuran (2 mL) was stirred for 13 hours at room temperature and atmospheric pressure under a hydrogen atmosphere. The mixture was filtered through Celite to remove the catalyst, and the filtrate was concentrated. A crude product of the title compound was obtained as a yellow oil. The crude product was used without purification for the following reaction.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d52b68919e9644048a02223bac15fb62
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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