Formaldehyde → N-(Hydroxymethyl)-5-nitropyridine-3-carboxamide

HRID 972757Notes

Reaction equation

HRID 972757 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[C:8]([CH:12]=1)[C:9]([NH2:11])=[O:10])([O-:3])=[O:2].[CH2:13]=[O:14]>CN(C)C=O>[OH:14][CH2:13][NH:11][C:9](=[O:10])[C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 132920255-Nitropyridine-3-carboxamide

Product 1

HCID 21405355N-(Hydroxymethyl)-5-nitropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g of 5-nitronicotinamide and 2ml of 37% formalin in 3 ml of dimethylformamide was stirred at 100° C. for 2 hours. After cooling, ice-water was added and the mixture was extracted with ethyl acetate. The extract was chromatographed over silica gel and recrystallized from ethanol to give 0.6 g of the desired product. mp 145° - 146° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe extract was chromatographed over silica gel
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-3527936925d74924bdece9eafe9dd2dd
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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