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

HRID 2232469노트

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HRID 2232469 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6348Carbon Disulfide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b80f249919f24051a42e6960b522e7d3
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04788213

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