6-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile → 6-Formyl-4-isobutyl-quinoline-3-carbonitrile

HRID 1297672Notes

Reaction equation

HRID 1297672 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]([C:13]#[N:14])[CH:6]2[CH2:15][CH:16]([CH3:18])[CH3:17]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:1]

Participants

4

Reactant 1

HCID 585857716-Hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile

Product 1

HCID 585858466-Formyl-4-isobutyl-quinoline-3-carbonitrileYield 56%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To the solution of 6-hydroxymethyl-4-isobutyl-1,4-dihydro-quinoline-3-carbonitrile (200 mg, 0.83 mmol) in chloroform (6 mL) was added manganese dioxide (300 mg). The mixture was stirred at reflux for 10 h. After removal of the solid by filtration, the filtrate was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0%-30% ethyl acetate in hexanes in 30 min) afforded 6-formyl-4-isobutyl-quinoline-3-carbonitrile (110 mg, 56%) as a white solid. LC-MS m/e 239 (MH+).

Workup

  1. temperatureat reflux for 10 h
  2. customAfter removal of the solid
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1154d6301b674925ae73ea6e38ed6be2
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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