1-(2-Chloro-8-fluoroquinolin-3-yl)ethanol → HCID 57707761, compound

HRID 1019787Notes

Reaction equation

HRID 1019787 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]([OH:14])[CH3:13])=[CH:10][C:9]2[C:4](=[C:5]([F:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1>[O-2].[O-2].[Mn+4].C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:11]([C:12](=[O:14])[CH3:13])=[CH:10][C:9]2[C:4](=[C:5]([F:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 1

HCID 577079711-(2-Chloro-8-fluoroquinolin-3-yl)ethanol

Product 1

HCID 57707761HCID 57707761, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a round-bottomed flask containing toluene (183 mL) was added 1-(2-chloro-8-fluoroquinolin-3-yl)ethanol (6.20 g, 27.5 mmol) and manganese dioxide (19.1 g, 220 mmol, 8 eq). The reaction was heated to reflux for 2 h, cooled to rt, filtered and concentrated. The product was diluted with hexanes and filtered to give as a white solid 1-(2-chloro-8-fluoroquinolin-3-yl)ethanone (4.43 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.40 (d, J=1.6 Hz, 1H), 7.71 (br d, J=8.2 Hz, 1H), 7.56 (td, J=7.8, 5.1 Hz, 1H), 7.54 (ddd, J=9.8, 7.8, 1.6 Hz, 1H). Mass Spectrum (ESI) m/e=223.9 (M+1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 2 h
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe product was diluted with hexanes
  6. filtrationfiltered

Sources & evidence

ORD record
ord-7185985600ea4d58848dce9bf708f12f
Source dataset
uspto-grants-2014_05
Patent number
US08716290B2

Reaction notes

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