Ethanolamine → N-(2-hydroxyethyl)-1-methyl-1H-pyrrole-2-carboxamide

HRID 437652Notes

Reaction equation

HRID 437652 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9]C)=O.[NH2:11][CH2:12][CH2:13][OH:14]>>[OH:14][CH2:13][CH2:12][NH:11][C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:9]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 142178Methyl 1-methylpyrrole-2-carboxylate

Product 1

HCID 21428972N-(2-hydroxyethyl)-1-methyl-1H-pyrrole-2-carboxamide

Procedure

A mixture of 5.5 parts of methyl 1-methyl-1H-pyrrole-2-carboxylate and 2.4 parts of 2-aminoethanol is stirred and refluxed for 2 hours. The reaction mixture is evaporated till dry. Benzene is added twice to the residue and evaporation is continued each time till dry. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions are collected and the eluent is evaporated. The residue is taken up in petroleumether and upon scratching, the product solidifies. It is filtered off and dried, yielding 1.9 parts of N-(2-hydroxyethyl)-1-methyl-1H-pyrrole-2-carboxamide; mp. 78.1° C.

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe reaction mixture is evaporated
  3. customtill dry
  4. additionBenzene is added twice to the residue and evaporation
  5. customtill dry
  6. customThe residue is purified by column-chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  8. customThe pure fractions are collected
  9. customthe eluent is evaporated
  10. filtrationIt is filtered off
  11. customdried

Sources & evidence

ORD record
ord-f88ceaab9ec8462d8f48e5e7beced937
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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