Ethyl Acetate → HCID 86671529, compound

HRID 2273187Notes

Reaction equation

HRID 2273187 reaction equation
[SH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][OH:13])=[CH:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.C(OCC)(=O)C>CC(C)=O.[O-2].[O-2].[Mn+4]>[SH:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[CH:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67246941HCID 67246941, compound

Product 1

HCID 86671529HCID 86671529, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

Manganese dioxide (1.38 g, 15.89 mmol) is added at room temperature to a stirred solution of (3-mercapto-6-methoxy-quinoline-4-yl)-methanol and its corresponding dimer (500 mg) in acetone (30 mL) and the resulting suspension is heated under reflux for 8 hours. The reaction mixture is then filtered through decalite and the filtrate is concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 2:1, v/v) to afford 3-mercapto-6-methoxy-quinoline-4-carbaldehyde and its corresponding dimer as a yellow solid (64 mg, 13% yield).

Workup

  1. temperaturethe resulting suspension is heated
  2. temperatureunder reflux for 8 hours
  3. filtrationThe reaction mixture is then filtered through decalite
  4. concentrationthe filtrate is concentrated
  5. customto give a residue that
  6. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-b447fd428cf641fbbaadae7160216e97
Source dataset
uspto-grants-2015_09
Patent number
US09120822B2

Reaction notes

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