Hexane → 5-Fluoro-3-hydroxy-6-methoxy-quinoline-4-carbaldehyde

HRID 2273203Notes

Reaction equation

HRID 2273203 reaction equation
[F:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH2:15][OH:16])=[C:5]([OH:14])[CH:6]=[N:7]2.C(OCC)(=O)C.CCCCCC>CC(C)=O.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([CH:15]=[O:16])=[C:5]([OH:14])[CH:6]=[N:7]2

Participants

6

Reactant 3

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 672487085-Fluoro-4-hydroxymethyl-6-methoxy-quinolin-3-ol

Product 1

HCID 866715305-Fluoro-3-hydroxy-6-methoxy-quinoline-4-carbaldehydeYield 42.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Conditions

Temperature
35 °C

Procedure

Manganese dioxide (299 mg, 4.3 mmol, 10.0 eq) is added at room temperature to a stirred solution of 5-fluoro-4-hydroxymethyl-6-methoxy-quinolin-3-ol (120 mg, 0.43 mmol, 1.0 eq) in acetone (12 mL) and the resulting mixture is stirred at 35° C. for 17 hours. The solid is filtered off, washed with acetone (3×10 mL) and the filtrate is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: ethyl acetate:hexane, 1:3, v/v) to afford 5-fluoro-3-hydroxy-6-methoxy-quinoline-4-carbaldehyde as a yellow solid (40 mg, 42% yield).

Workup

  1. filtrationThe solid is filtered off
  2. washwashed with acetone (3×10 mL)
  3. concentrationthe filtrate is concentrated
  4. customto give a residue that
  5. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-e5b620699e474d298afdcaad7ca92ba9
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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