Ammonium Chloride → 2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenylamine

HRID 32133Notes

Reaction equation

HRID 32133 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[N+:16]([O-])=O)=[CH:4][CH2:3]1.[Cl-].[NH4+]>C(O)C.[Cl-].[Na+].O.[Fe]>[CH3:1][C:2]1([CH3:19])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=2[NH2:16])=[CH:4][CH2:3]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 231415961-(4,4-Dimethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

Product 1

HCID 231419942-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenylamineYield 108.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4,4-dimethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene (3.5 g, 13.4 mmol) prepared in Example (1c) in ethanol (30 mL) were added a solution (5 mL) of aqueous ammonium chloride (2.9 g, 54 mmol) and iron powder (1.5 g, 26.8 mmol), and the mixture was stirred at an external temperature of 90° C. for 1 hour and 30 minutes. The reaction mixture was passed through Celite, brine was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the desiccant was filtered off. The filtrate was concentrated under reduced pressure to give 3.35 g of the title compound as a yellow oil.

Workup

  1. additionwas added to the filtrate
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b89476f2916245b5a2da8678d6e17602
Source dataset
uspto-grants-2008_09
Patent number
US07425554B2

Reaction notes

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