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

HRID 2218789Notes

Reaction equation

[CH2:1]([C:3]1([CH2:20][CH3:21])[CH2:8][CH2:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[N+:17]([O-])=O)=[CH:5][CH2:4]1)[CH3:2].[Cl-].[NH4+]>C(O)C.[Fe]>[CH2:20]([C:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[NH2:17])=[CH:5][CH2:4]1)[CH3:21]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 1-(4,4-diethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene (2.4 g, 8.3 mmol) prepared in Example (6d) in ethanol (20 mL) were added an aqueous solution (5 mL) of ammonium chloride (2.2 g, 41 mmol) and iron powder (1.2 g, 20.7 mmol), and the mixture was stirred at an external temperature of 90° C. for 1 hour. The reaction mixture was passed through Celite for filtration, and then brine was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered off, and then the filtrate was concentrated under reduced pressure to give 2.6 g of the title compound as a yellow oil.

Workup

filtrationThe reaction mixture was passed through Celite for filtration
additionbrine was added to the filtrate
extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationthe desiccant was filtered off
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-9cd217caaf6f4beb8038620e376f9d73
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410971B2

Reaction notes

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