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

HRID 703445ノート

反応式

HRID 703445 の反応式
[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

参加物

6

反応物 3

HCID 962WaterHCID 14873016HCID 14873016、化合物HCID 21226445Aluminium lithium hydride

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-13c1d5f08935442ca892b8b1dc894fd5
出典データセット
uspto-grants-1991_01
特許番号
US04983607

反応ノート

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