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

HRID 969461Notes

Reaction equation

HRID 969461 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([C:20](=[O:23])[CH2:21]Cl)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].[OH-].[Na+].[Cl-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[C:11]([CH:20]2[CH2:21][O:23]2)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

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 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.0 g (18.3 mmol) 7-benzyloxy-5-(2-chloro-acetyl)-1H-quinolin-2-one are placed in 150 mL tetrahydrofuran and at 0 to 5° C. combined with 434 mg (819.9 mmol) lithium borohydride. The mixture is stirred for 30 minutes, then 43 mL of a 2.5 molar sodium hydroxide solution are added and the mixture is stirred for a further 4 hours with heating to ambient temperature. The mixture is combined with sodium chloride solution, filtered and extracted repeatedly with ethyl acetate/tetrahydrofuran (1:1). The solid filtered off and the organic phases are combined and freed from the solvent. The residue is suspended in methanol, suction filtered and dried. Yield 4.8 g (89%); mass spectroscopy: [M+H]+=294.

Workup

  1. stirringthe mixture is stirred for a further 4 hours
  2. filtrationfiltered
  3. extractionextracted repeatedly with ethyl acetate/tetrahydrofuran (1:1)
  4. filtrationThe solid filtered off
  5. filtrationsuction filtered
  6. customdried

Sources & evidence

ORD record
ord-dcfc32204d304fb189880a45b0ee0aff
Source dataset
uspto-grants-2007_12
Patent number
US07307076B2

Reaction notes

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