Aluminum(III) Chloride → 4,4-Dimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 1382915Notes

Reaction equation

HRID 1382915 reaction equation
[CH3:1][C:2]([CH3:13])=[CH:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-]>>[CH3:1][C:2]1([CH3:13])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:4](=[O:5])[CH2:3]1

Participants

3

Reactant 2

HCID 6451240Aluminum(III) Chloride2×HCID 123870223-Methyl-N-phenylbut-2-enamide

Product 1

HCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-oneYield 61.5%

Conditions

Temperature
85 °C

Procedure

To 40 g (0.22 mol) of 3-methylcrotonoanilide, heated in the molten state at 130° C., was added 33.4 g (0.25 mol) of aluminum chloride, portionwise, over a 30 minute period. Heating was continued at 130° C. for a further 30 minutes, and then the temperature was lowered to 85° C. and a further 5 g (0.038 mol) of aluminum chloride was added. The temperature was maintained at 85° C. for 1 hour and then the reaction mixture was treated cautiously with 500 g of ice. The resulting mixture was extracted with ether and the ether extracts were dried (MgSO4) and evaporated in vacuo. The residue was chromatographed on silicic acid, eluting with ether:hexane (1:2), and the product containing fractions were combined and evaporated in vacuo. This afforded 23.7 g (59% yield) of the title compound, mp 111°-112° C.

Workup

  1. temperatureHeating
  2. waitwas continued at 130° C. for a further 30 minutes
  3. customwas lowered to 85° C.
  4. extractionThe resulting mixture was extracted with ether
  5. dry with materialthe ether extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silicic acid
  8. washeluting with ether:hexane (1:2)
  9. additionthe product containing fractions
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-3b0100e3a40f48c9b2ba0e6973c28215
Source dataset
uspto-grants-1989_02
Patent number
US04808597

Reaction notes

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