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

HRID 2232469Notes

Reaction equation

HRID 2232469 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 aluminium 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-b80f249919f24051a42e6960b522e7d3
Source dataset
uspto-grants-1988_11
Patent number
US04788213

Reaction notes

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