4-(hydroxymethyl)-N-methylpyridine-2-carboxamide hydrochloride hydrate → 4-formyl-N-methylpicolinamide

HRID 714448Notes

Reaction equation

HRID 714448 reaction equation
O.Cl.[OH:3][CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[CH:6]=1>CO.[O-2].[O-2].[Mn+4]>[CH:4]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[CH:6]=1)=[O:3]

Participants

4

Reactant 1

HCID 666313824-(hydroxymethyl)-N-methylpyridine-2-carboxamide hydrochloride hydrate

Product 1

HCID 219638894-formyl-N-methylpicolinamide

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 887MethanolSolvent

Procedure

7.50 g (33.989 mmol) of 4-(hydroxymethyl)-N-methylpyridine-2-carboxamide hydrochloride hydrate (Example 40A) were initially charged in 90 ml of methanol, 23.64 g (271.915 mmol) of manganese dioxide were added and the mixture was stirred at RT overnight. The reaction mixture was filtered off with suction through silica gel, the silica gel/manganese dioxide mixture was stirred with tetrahydrofuran/methanol 1:1 overnight, the silica gel/manganese dioxide mixture was then filtered off and the filtrate was evaporated.

Workup

  1. filtrationThe reaction mixture was filtered off with suction through silica gel
  2. stirringthe silica gel/manganese dioxide mixture was stirred with tetrahydrofuran/methanol 1:1 overnight
  3. filtrationthe silica gel/manganese dioxide mixture was then filtered off
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-adac596412354eaba9b89de9a01c459b
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

Loading…