Lithium borohydride → 3,4-dihydro-4-(2-hydroxyethyl)-6-methoxy-1-methyl-2(1H)-quinolinone

HRID 2372022Notes

Reaction equation

HRID 2372022 reaction equation
[BH4-].[Li+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10](=[O:16])[CH2:9][CH:8]2[CH2:17][C:18](OC)=[O:19]>O1CCCC1>[OH:19][CH2:18][CH2:17][CH:8]1[C:7]2[C:12](=[CH:13][CH:14]=[C:5]([O:4][CH3:3])[CH:6]=2)[N:11]([CH3:15])[C:10](=[O:16])[CH2:9]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 15678870HCID 15678870, compound

Product 1

HCID 156788713,4-dihydro-4-(2-hydroxyethyl)-6-methoxy-1-methyl-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium borohydride (100 ml of a 2.0M solution in tetrahydrofuran) was added to a solution of 34.6 g of 1,2,3,4-tetrahydro-6-methoxy-1-methyl-2-oxo-4-quinoline acetic acid, methyl ester in 330 ml of tetrahydrofuran. The mixture was stirred at room temperature for 84 hours, cooled to 0° C., quenched with 10% aqueous hydrochloric acid, and concentrated. The aqueous layer was basified with potassium carbonate and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford 3,4-dihydro-4-(2-hydroxyethyl)-6-methoxy-1-methyl-2(1H)-quinolinone.

Workup

  1. temperaturecooled to 0° C.
  2. customquenched with 10% aqueous hydrochloric acid
  3. concentrationconcentrated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2c3a94cb6a184986b58b076d6b99a224
Source dataset
uspto-grants-1992_03
Patent number
US05097033

Reaction notes

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