HCID 67406221, compound → HCID 86680272, compound

HRID 571041Notes

Reaction equation

HRID 571041 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH2:27][OH:28])[N:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:10](=[O:29])[CH:11]=[C:12]([CH:27]=[O:28])[N:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67406221HCID 67406221, compound

Product 1

HCID 86680272HCID 86680272, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

5-(Benzyloxy)-1-(biphenyl-3-yl)-2-(hydroxymethyl)pyridin-4(1H)-one (112 g, 292 mmol) was dissolved in 2.2 L of anhydrous THF and active manganese dioxide (407 g, 4.68 mol) was added. The reaction mixture was heated under reflux for 3 hours. The insoluble part was filtered off and the filtrate was concentrated to give crude 5-(benzyloxy)-1-(biphenyl-3-yl)-4-oxo-1,4-dihydropyridine-2-carbaldehyde, which was used in next step without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. filtrationThe insoluble part was filtered off
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-655f20c9191649eca8be7dd26a601921
Source dataset
uspto-grants-2015_05
Patent number
US09024032B2

Reaction notes

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