Ammonia → (2-Aminocyclohex-1-en-1-yl)(4-methylphenyl)methanone

HRID 1906424Notes

Reaction equation

HRID 1906424 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=O)=[O:8])=[CH:3][CH:2]=1.[N+:17]([O-])([O-])=O.[NH4+].N>>[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([C:7]([C:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[NH2:17])=[O:8])=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 22985Ammonium nitrateHCID 11218191HCID 11218191, compound

Product 1

HCID 13504838(2-Aminocyclohex-1-en-1-yl)(4-methylphenyl)methanoneYield 76%

Procedure

Ammonia gas was bubbled into a cooled flask containing a suspension mixture of 2-p-toluoylcyclohexanone (21.6 g, 0.1 mole) and 8.8 g (0.11 mole) of ammonium nitrate until 17 g (1 mole) of ammonia was absorbed. The flask was stoppered and the mixture stirred for 30 min when a solution resulted. The flask and its mixture was allowed to stand overnight and the resulting brown solution was evaporated. The residue was extracted with boiling diethyl ether, 4×250 ml portions, filtered, and the extract was concentrated until crystallization began in the hot, and the mixture was allowed to cool. A total of 10 g of pale yellow needle crystals was obtained, mp 130°-131° C. A second crop of 6.35 g, mp 129°-130.5° C., for a total of 76% yield was obtained. The UV, mass spectrum and NMR spectra were consistent with the sub-titled intermediate amine.

Workup

  1. customAmmonia gas was bubbled into a cooled flask
  2. additioncontaining
  3. customwas absorbed
  4. customresulted
  5. waitto stand overnight
  6. customthe resulting brown solution was evaporated
  7. extractionThe residue was extracted with boiling diethyl ether, 4×250 ml portions
  8. filtrationfiltered
  9. concentrationthe extract was concentrated until crystallization
  10. temperatureto cool

Sources & evidence

ORD record
ord-1282706160fd47e7995f4b4b1ab9265e
Source dataset
uspto-grants-1987_03
Patent number
US04652559

Reaction notes

Loading…