4-Hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one → 1-(3-Chloro-phenyl)-2-oxo-1,2-dihydro-pyridine-4-carbaldehyde

HRID 2289641Notes

Reaction equation

HRID 2289641 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[C:5](=[O:16])[CH:4]=1>C(Cl)Cl.O=[Mn]=O>[Cl:15][C:11]1[CH:10]=[C:9]([N:6]2[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][C:5]2=[O:16])[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 186987734-Hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one

Product 1

HCID 186987831-(3-Chloro-phenyl)-2-oxo-1,2-dihydro-pyridine-4-carbaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxymethyl-1-(3-chlorophenyl)-1H-pyridin-2-one (2.39 g, 10.14 mmol) in CH2Cl2 (250 ml) was added MnO2 (4.41 g, 50.71 mmol) and stirred for 18 hours. The suspension was filtered through celite and the pad washed with additional CH2Cl2 (200 ml). The combined filtrates were evaporated in vacuo and chromatographed (silica gel, 5-20% EtOAc: CH2Cl2 gradient elution) to afford the title compound.

Workup

  1. filtrationThe suspension was filtered through celite
  2. washthe pad washed with additional CH2Cl2 (200 ml)
  3. customThe combined filtrates were evaporated in vacuo
  4. customchromatographed
  5. wash(silica gel, 5-20% EtOAc: CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-8092fa023ba84a0997d2cb42ad3da008
Source dataset
uspto-grants-2000_07
Patent number
US06093737

Reaction notes

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