6-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one → 6-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one

HRID 1023180Notes

Reaction equation

HRID 1023180 reaction equation
[Br:1][CH2:2][CH:3]([OH:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:2][C:3](=[O:17])[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11](=[O:16])[CH2:10][CH2:9]2

Participants

4

Reactant 2

HCID 866804246-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-oneHCID 178418287HCID 178418287, compound

Product 1

HCID 866804256-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 6-(3-bromo-2-hydroxypropoxy)-3,4-dihydroquinolin-2(1H)-one (0.2 g, 0.666 mmol) in DCM was added 4 Å molecular sieves powder (0.2 g) and pyridinium chlorochromate (0.287 g, 1.333 mmol). The reaction mixture was stirred at room temperature for 12 h. The reaction mixture was filtered through celite and washed with DCM (50 mL). The filtrate was concentrated and the crude product purified by flash chromatography on silica gel using 60% ethyl acetate in hexane to give 6-(3-bromo-2-oxopropoxy)-3,4-dihydroquinolin-2(1H)-one as an off white solid (0.15 g, 76%). LCMS: RT 0.67 min; LCMS (ES-API), m/z 298.0 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with DCM (50 mL)
  3. concentrationThe filtrate was concentrated
  4. customthe crude product purified by flash chromatography on silica gel using 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-df2be4796c5c48f785fdf3628b55066d
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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