Hexane → 3-Hydroxy-6-methoxy-quinoline-4-carbaldehyde

HRID 2273178Notes

Reaction equation

HRID 2273178 reaction equation
[OH:1][CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][C:4]=1[OH:15].CCCCCC>CC(C)=O.[O-2].[O-2].[Mn+4]>[OH:15][C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:3]=1[CH:2]=[O:1])=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2

Participants

5

Reactant 2

HCID 8058HexaneHCID 672464714-Hydroxymethyl-6-methoxy-quinoline-3-ol

Product 1

HCID 866715273-Hydroxy-6-methoxy-quinoline-4-carbaldehydeYield 55.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent2×

Procedure

Manganese dioxide (650 mg, 7.5 mmol, 10.0 eq) is added at room temperature to a stirred solution of 4-hydroxymethyl-6-methoxy-quinoline-3-ol (220 mg, 0.75 mmol, 1.0 eq) in acetone (30 mL). After 2 hours stirring at room temperature, the reaction mixture is filtered through decalite and the filtrate is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: hexane:acetone, 1:1, v/v) to afford 3-hydroxy-6-methoxy-quinoline-4-carbaldehyde as a yellow solid (85 mg, 34% yield).

Workup

  1. filtrationthe reaction mixture is filtered through decalite
  2. concentrationthe filtrate is concentrated
  3. customto give a residue that
  4. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-f18749b819f44ed58b8b8e1b351f8230
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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