Sodium Chloride → 7-benzyloxy-5-oxiranyl-1H-quinolin-2-one

HRID 1867325Notes

Reaction equation

HRID 1867325 reaction equation
[BH4-].[Li+].[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17](=[O:21])[NH:18]2)=[C:13]([C:22](=[O:25])[CH2:23]Cl)[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+].[Cl-].[Na+]>C1COCC1.C(O)(=O)C>[CH2:3]([O:10][C:11]1[CH:20]=[C:19]2[C:14]([CH:15]=[CH:16][C:17](=[O:21])[NH:18]2)=[C:13]([CH:22]2[CH2:23][O:25]2)[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 210728597-(Benzyloxy)-5-(chloroacetyl)quinolin-2(1H)-one

Product 1

HCID 574693717-benzyloxy-5-oxiranyl-1H-quinolin-2-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (434 mg, 19.93 mmol) is added to a suspension of 7-benzyloxy-5-(2-chloroacetyl)-1H-quinolin-2-one (6 g, 18.31 mmol) in THF (150 mL) at 0° C.-5° C. and the mixture is stirred for 30 minutes. 2.5 N sodium hydroxide solution (43 mL, 107.50 mmol) is added and the mixture is stirred for 2 hours at 5° C.-10° C. and for 2.5 hours at ambient temperature. Then the reaction mixture is slowly combined with glacial acetic acid (6.5 mL) followed by semisaturated sodium chloride solution (100 mL) and stirred for a further 5 minutes. The precipitate formed is filtered off and the aqueous phase is extracted with ethyl acetate/THF (1/1.5×100 mL). The solid filtered off and the organic phases are combined, dried with sodium sulfate, and evaporated down. The crude product is stirred with methanol (30 mL) and the precipitate is filtered off and dried at ambient temperature. Yield: 4.8 g (89%); mass spectroscopy: [M+H]+=294.

Workup

  1. stirringthe mixture is stirred for 2 hours at 5° C.-10° C. and for 2.5 hours at ambient temperature
  2. stirringstirred for a further 5 minutes
  3. customThe precipitate formed
  4. filtrationis filtered off
  5. extractionthe aqueous phase is extracted with ethyl acetate/THF (1/1.5×100 mL)
  6. filtrationThe solid filtered off
  7. dry with materialdried with sodium sulfate
  8. customevaporated down
  9. stirringThe crude product is stirred with methanol (30 mL)
  10. filtrationthe precipitate is filtered off
  11. customdried at ambient temperature

Sources & evidence

ORD record
ord-535023d492b247c29ce7da4aa062d9ef
Source dataset
uspto-grants-2009_12
Patent number
US07632834B2

Reaction notes

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