1-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one → 1-(4-Chlorobenzyl)-5-(3-methoxybenzoyl)pyridin-2(1H)-one

HRID 1948204Notes

Reaction equation

HRID 1948204 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([CH:13]([OH:22])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH:10]=[CH:9][C:8]2=[O:23])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[C:11]([C:13](=[O:22])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=3)[CH:10]=[CH:9][C:8]2=[O:23])=[CH:24][CH:25]=1

Participants

4

Reactant 1

HCID 589669561-(4-chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)methyl)pyridin-2(1H)-one

Product 1

HCID 589669171-(4-Chlorobenzyl)-5-(3-methoxybenzoyl)pyridin-2(1H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

According to Scheme 7 Method C: 1-(4-Chlorobenzyl)-5-(hydroxy(3-methoxyphenyl)-methyl)pyridin-2(1H)-one (1 eq, 0.28 mmol, 0.10 g, Example 41) and manganese dioxide (30 eq, 8.43 mmol, 0.73 g) were stirred overnight at room temperature in CH2Cl2 (10 mL). Upon completion, the crude mixture was filtered through a pad of celite and the filtrate was concentrated. The crude residue was partitioned between water and CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over MgSO4 and concentrated under vacuum to afford the title compound as a white solid (0.28 mmol, 0.10 g, 100%).

Workup

  1. filtrationUpon completion, the crude mixture was filtered through a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe crude residue was partitioned between water and CH2Cl2
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-282e05f832c9466aa59d2d81b6d752d1
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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