3-Hydroxymethyl-6-methyl-2-(3-nitrophenylamino)pyridine → 6-Methyl-2-(3-nitrophenylamino)nicotinaldehyde

HRID 478723Notes

Reaction equation

HRID 478723 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:9][C:6]1[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-:19])=[O:18])[CH:12]=2)[N:5]=1

Participants

4

Reactant 1

HCID 180026193-Hydroxymethyl-6-methyl-2-(3-nitrophenylamino)pyridine

Product 1

HCID 180026466-Methyl-2-(3-nitrophenylamino)nicotinaldehydeYield 72.1%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a suspension of 3-hydroxymethyl-6-methyl-2-(3-nitrophenylamino)pyridine (11.05 g, 42.62 mmol) in chloroform (200 ml) was added manganese dioxide (50 g), and the mixture was stirred overnight and filtered to remove an insoluble. Evaporation of the solvent from the filtrate gave a residue. Recrystallization of the resultant residue from acetonitrile gave 6-methyl-2-(3-nitrophenylamino)nicotinaldehyde (7.90 g, 72%).

Workup

  1. filtrationfiltered
  2. customto remove an insoluble
  3. customEvaporation of the solvent from the filtrate
  4. customgave a residue
  5. customRecrystallization of the resultant residue from acetonitrile

Sources & evidence

ORD record
ord-27e4b59d605b442da1fed7f5e375c992
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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