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

HRID 2232469ノート

反応式

HRID 2232469 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6348Carbon Disulfide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b80f249919f24051a42e6960b522e7d3
出典データセット
uspto-grants-1988_11
特許番号
US04788213

反応ノート

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