Diethyl Ether → 1-(Isoquinolin-1-yl)ethan-1-one

HRID 1637754

반응식

HRID 1637754 반응식
[CH3:1][Mg]Br.CC[O:6][CH2:7][CH3:8].C1(C#N)[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1>O1CCCC1>[C:7]([C:8]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][N:10]=1)(=[O:6])[CH3:1]

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 3060571-IsoquinolinecarbonitrileHCID 178418573HCID 178418573, 화합물

생성물 1

HCID 131572141-(Isoquinolin-1-yl)ethan-1-one수율 62%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Methyl magnesium bromide in ether (8.1 ml, 24.3 mmole) is dissolved in 16 ml tetrahydrofuran in an oven dried 100 ml two neck round bottom flask under nitrogen. The solution is cooled to 0° C., is diluted with 8 ml diethyl ether, and is treated with 1-isoquinoline carbonitrile (3.0 g, 19.5 mmole). The reaction is warmed to reflux for one hour, is cooled to 0° C., and is quenched with 20 ml 6 M hydrochloric acid. The reaction mixture is warmed to 50° C. for two hours, is cooled, and is poured into 75 ml 2N sodium hydroxide. The mixture is extracted with 3×80 ml ethyl acetate and the combined organics are dried over potassium carbonate. The dried organics are concentrated in vacuo to a crude amber oil. The crude material is chromatographed over 150 g silica gel (230-400 mesh), eluting with 10% acetone/hexane, while collecting 22 ml fractions. Fractions 16-26 are combined and concentrated to provide 2.1 g (62%) of 1-acetylisoquinoline.

후처리

  1. dry with materialdried 100 ml two neck round bottom flask under nitrogen
  2. additionis diluted with 8 ml diethyl ether
  3. temperatureThe reaction is warmed
  4. temperatureto reflux for one hour
  5. temperatureis cooled to 0° C.
  6. customis quenched with 20 ml 6 M hydrochloric acid
  7. temperatureThe reaction mixture is warmed to 50° C. for two hours
  8. temperatureis cooled
  9. additionis poured into 75 ml 2N sodium hydroxide
  10. extractionThe mixture is extracted with 3×80 ml ethyl acetate
  11. dry with materialthe combined organics are dried over potassium carbonate
  12. concentrationThe dried organics are concentrated in vacuo to a crude amber oil
  13. customThe crude material is chromatographed over 150 g silica gel (230-400 mesh)
  14. washeluting with 10% acetone/hexane
  15. customwhile collecting 22 ml fractions
  16. concentrationconcentrated

출처 및 근거

ORD 기록
ord-09329fcf14b84744a898443ecf5a5188
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06043248

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