Ethyl Acetate → 3-Chloro-5-fluoro-6-methoxy-quinoline-4-carbaldehyde

HRID 633828Notes

Reaction equation

HRID 633828 reaction equation
[B-](F)(F)(F)F.[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+]([F:21])(CC2)C1.[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:32]=1[CH:33]=[O:34])=[CH:30][C:29]([O:35][CH3:36])=[CH:28][CH:27]=2.C(OCC)(=O)C>C(#N)C>[Cl:22][C:23]1[CH:24]=[N:25][C:26]2[C:31]([C:32]=1[CH:33]=[O:34])=[C:30]([F:21])[C:29]([O:35][CH3:36])=[CH:28][CH:27]=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724933SelectfluorHCID 859847983-Chloro-6-methoxyquinoline-4-carbaldehyde

Product 1

HCID 867307093-Chloro-5-fluoro-6-methoxy-quinoline-4-carbaldehydeYield 57.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
10 °C

Procedure

Selectfluor (2.4 g, 6.77 mmol, 1.5 eq) is added at 10° C. to a stirred solution of 3-chloro-6-methoxy-quinoline-4-carbaldehyde (1.0 g, 4.5 mmol, 1.0 eq) in acetonitrile (50 mL). After 24 hours stirring at 10° C., the reaction mixture is extracted with ethyl acetate (3×100 mL) and brine (50 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 10:1 to 5:1, v/v) to afford 3-chloro-5-fluoro-6-methoxy-quinoline-4-carbaldehyde as a yellow solid (620 mg, 57% yield).

Workup

  1. extractionthe reaction mixture is extracted with ethyl acetate (3×100 mL) and brine (50 mL)
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-2139ad054e65485aafcc397ce885c302
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

Loading…