Epichlorohydrin → HCID 18433024, compound

HRID 2305546Notes

Reaction equation

HRID 2305546 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH:8]=[C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10]2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[CH2:26]([CH:28]1[O:30][CH2:29]1)Cl>CN(C=O)C.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:19][CH2:26][CH:28]3[CH2:29][O:30]3)=[CH:8][C:9]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 2897437-Methoxy-2-phenyl-quinolin-4-ol

Product 1

HCID 18433024HCID 18433024, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 7-methoxy-2-phenyl-1H-quinolin-4-one (1.5 g, 6 mmol) in DMF (11 ml) were added successively K2CO3 (1.66 g, 12 mmol) and (RS)-epichlorohydrin (1.9 ml, 24 mmol). The reaction mixture was stirred at 65° C. for 3 hours, then cooled to room temperature and diluted with CH2Cl2 (25 ml). Solid was filtrated, and filtrate was concentrated. The residue was chromatographed over silica gel (hexane-ethyl acetate, 4:1) to provide (RS)-7-methoxy-4-oxiranylmethoxy-2-phenyl-quinoline (1.05 g, 57%) as a colorless oil, MS: m/e=307 (M+).

Workup

  1. temperaturecooled to room temperature
  2. filtrationSolid was filtrated
  3. concentrationfiltrate was concentrated
  4. customThe residue was chromatographed over silica gel (hexane-ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-167eed1f5a1c4d19afe2c9bf8b24695f
Source dataset
uspto-grants-2002_08
Patent number
US06440995B1

Reaction notes

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