Acetyl chloride → 6-Acetyl-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-one

HRID 2118526Notes

Reaction equation

HRID 2118526 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([CH3:13])([CH3:12])[CH2:4][C:3]1=[O:14].[Cl-].[Al+3].[Cl-].[Cl-].[C:19](Cl)(=[O:21])[CH3:20]>C(=S)=S>[C:19]([C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[N:2]([CH3:1])[C:3](=[O:14])[CH2:4][C:5]2([CH3:12])[CH3:13])(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 140102511,4,4-Trimethyl-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 134781666-Acetyl-1,4,4-trimethyl-3,4-dihydroquinolin-2(1H)-oneYield 74.2%

Reagents, catalysts & solvents 1

HCID 6348Carbon DisulfideSolvent

Procedure

21.5 g of 3,4-dihydro-1,4,4-trimethyl-2(1H)-quinolinone were dissolved in 43 g of carbon disulphide and the solution was treated with 85 g of aluminum chloride. 17.8 g of acetyl chloride were slowly added dropwise thereto while cooling with ice and stirring vigorously. The mixture was subsequently heated at reflux for 1.5 hours, cooled and treated cautiously with ice-water. The resulting mixture was extracted three times with ethyl acetate and the ethyl acetate extracts were washed with water, dried and evaporated. The thus-obtained brownish oil was filtered over silica gel [eluting agent: hexane/ethyl acetate (2:1)] and then recrystallized from hexane/ethyl acetate. There were obtained 19.5 g of 6-acetyl-3,4-dihydro-1,4,4-trimethyl-2(1H)-quinolinone in the form of colourless crystals of melting point 75°-77° C.

Workup

  1. temperaturewhile cooling with ice
  2. temperatureThe mixture was subsequently heated
  3. temperatureat reflux for 1.5 hours
  4. temperaturecooled
  5. extractionThe resulting mixture was extracted three times with ethyl acetate
  6. washthe ethyl acetate extracts were washed with water
  7. customdried
  8. customevaporated
  9. filtrationThe thus-obtained brownish oil was filtered over silica gel [eluting agent: hexane/ethyl acetate (2:1)]
  10. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-66b1afcd4574447c908040e76f384ace
Source dataset
uspto-grants-1987_07
Patent number
US04678793

Reaction notes

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