Water → (+/-)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone

HRID 703445노트

반응식

HRID 703445 반응식
[O:1]=[C:2]1[CH2:11][CH:10]([CH2:12][C:13](OC)=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCOCC1.CCOCC>[OH:14][CH2:13][CH2:12][CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3][C:2](=[O:1])[CH2:11]1

참가 물질

6

반응물 3

HCID 962WaterHCID 14873016HCID 14873016, 화합물HCID 21226445Aluminium lithium hydride

생성물 1

HCID 14624972(+/-)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone수율 55.4%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 312751,4-Dioxane용매

실험 절차

A solution of 11 g (0.05 mol) of methyl (±)-2-oxo-1,2,3,4-tetrahydro-4-quinolineacetate in 50 ml of dioxane is poured dropwise while stirring under an inert atmosphere into a suspension of 2.65 g (0.07 mol) of lithium aluminium hydride in 250 ml of dry ether. The mixture is then heated for 4 h to reflux. After cooling, the reaction is hydrolysed by the slow addition of 10 ml of water with vigorous stirring. The suspension is filtered and the inorganic solid is washed with 20 ml of dioxane. The filtrate is evaporated and the oil obtained is ground in ether, causing it to crystallize. The solid is recrystallized in ethyl acetate. 5.3 g (55%) of (±)-4-(2-hydroxyethyl)-3,4-dihydro-2(1H)-quinolinone, melting point 119°-120° C., are obtained.

후처리

  1. temperatureThe mixture is then heated for 4 h
  2. temperatureto reflux
  3. temperatureAfter cooling
  4. filtrationThe suspension is filtered
  5. washthe inorganic solid is washed with 20 ml of dioxane
  6. customThe filtrate is evaporated
  7. customthe oil obtained
  8. customto crystallize
  9. customThe solid is recrystallized in ethyl acetate

출처 및 근거

ORD 기록
ord-13c1d5f08935442ca892b8b1dc894fd5
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04983607

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