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

HRID 401373Notes

Reaction equation

HRID 401373 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[C:5]1([NH:11][C:12](=[O:17])[CH:13]=[C:14]([CH3:16])[CH3:15])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1C=CC=CC=1>[CH3:16][C:14]1([CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:11][C:12](=[O:17])[CH2:13]1

Participants

4

Reactant 2

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

Product 1

HCID 142099454,4-Dimethyl-3,4-dihydroquinolin-2(1H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

AlCl3 (500 g, 3.8 mol) was carefully added to a suspension of 3-methyl-but-2-enoic acid phenylamide (105 g, 0.6 mol) in benzene (1000 mL). The reaction mixture was stirred at 80° C. overnight and poured into ice-water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (250 mL×3). The combined organic layers were washed with water (200 mL×2) and brine (200 mL), dried over Na2SO4 and concentrated to give 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (90 g, 86%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (250 mL×3)
  3. washThe combined organic layers were washed with water (200 mL×2) and brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a04401b89ab947e3b0335b46eb515202
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

Loading…