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

HRID 703445Notes

Reaction equation

HRID 703445 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-13c1d5f08935442ca892b8b1dc894fd5
Source dataset
uspto-grants-1991_01
Patent number
US04983607

Reaction notes

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