Ethanolamine → N-(2-Hydroxyethyl)-2-methyl-5-nitropyridine-3-carboxamide

HRID 972752Notes

Reaction equation

HRID 972752 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[NH2:16][CH2:17][CH2:18][OH:19]>C(O)C>[OH:19][CH2:18][CH2:17][NH:16][C:4](=[O:6])[C:3]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[N:12][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 287239Ethyl 2-methyl-5-nitronicotinate

Product 1

HCID 54034267N-(2-Hydroxyethyl)-2-methyl-5-nitropyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 2-methyl-5-nitronicotinate (1 g.) and 2-aminoethanol (4 ml.) in ethanol (5ml.) was stirred at room temperature for 16 hours. The solvent was distilled off, the residue was purified by silica gel chromatography and recrystallized from ethyl acetate n-hexane to give the desired yellow crystals. mp 144° - 145° C.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was purified by silica gel chromatography
  3. customrecrystallized from ethyl acetate n-hexane
  4. customto give the desired yellow crystals

Sources & evidence

ORD record
ord-e50f24c5f5de465a89c287c68e8b8281
Source dataset
uspto-grants-1977_10
Patent number
US04053608

Reaction notes

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