alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-pyridinemethanol → 3,4-Dimethoxy-5-nitrophenyl 2-pyridyl ketone

HRID 274500Notes

Reaction equation

HRID 274500 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[OH:15])[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]=1[O:9][CH3:10]>CC(C)=O.[O-2].[O-2].[Mn+4]>[N:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:14]([C:5]1[CH:6]=[C:7]([N+:11]([O-:13])=[O:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15]

Participants

4

Reactant 1

HCID 21459111alpha-(3,4-Dimethoxy-5-nitrophenyl)-2-pyridinemethanol

Product 1

HCID 179777233,4-Dimethoxy-5-nitrophenyl 2-pyridyl ketone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 180AcetoneSolvent

Procedure

7 g of manganese dioxide and added portionwise to 4.0 g of α-(3,4-dimethoxy-5-nitrophenyl)-2-pyridine-methanol dissolved in 100 ml of acetone while constantly heating under reflux over a period of 2.5 hours. Thereupon, the mixture is heated under reflux for an additional 2 hours. The manganese salts are subsequently filtered and the residue obtained after evaporation is recrystallized from ether/hexane. There is obtained 3,4-dimethoxy-5-nitrophenyl 2-pyridyl ketone of m.p. 113°.

Workup

  1. temperaturewhile constantly heating
  2. temperatureunder reflux over a period of 2.5 hours
  3. temperatureThereupon, the mixture is heated
  4. temperatureunder reflux for an additional 2 hours
  5. filtrationThe manganese salts are subsequently filtered
  6. customthe residue obtained
  7. customafter evaporation
  8. customis recrystallized from ether/hexane

Sources & evidence

ORD record
ord-793faa31426341a1adbfcfbdeb12836b
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Reaction notes

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