Ethanol → N-Ethylisonicotinamide

HRID 638305Notes

Reaction equation

HRID 638305 reaction equation
C(O)C.[CH2:4]([NH2:6])[CH3:5].[C:7](OC)(=[O:14])[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1>O>[CH2:4]([NH:6][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)[CH3:5]

Participants

5

Reactant 3

HCID 702EthanolHCID 6341EthylamineHCID 227085Methyl isonicotinate

Product 1

HCID 571600N-Ethylisonicotinamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 200 ml of ethanol and 20 ml water was cooled in an ice bath and saturated with ethylamine for 0.5 hr. then 80 g of crude methyl isonicotinate was added with cooling. Ethylamine was again bubbled onto the reaction mixture for 10 min and then it was allowed to stand overnight at room temperature. It was then concentrated in vacuo to leave 82.82 g of a pale oil which became semisolid on cooling.

Workup

  1. temperaturewith cooling
  2. customEthylamine was again bubbled onto the reaction mixture for 10 min
  3. concentrationIt was then concentrated in vacuo

Sources & evidence

ORD record
ord-9cbaf1315d844d779728f10b59c9163a
Source dataset
uspto-grants-1985_12
Patent number
US04560692

Reaction notes

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