Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile

HRID 241687Notes

Reaction equation

HRID 241687 reaction equation
[NH2:1]/[C:2](/[CH3:6])=[CH:3]/[C:4]#[N:5].C[O:8][C:9](=O)[C:10]#[CH:11].C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>CN(C=O)C>[CH3:6][C:2]1[NH:1][C:9](=[O:8])[CH:10]=[CH:11][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 13536Methyl propiolateHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 53247203-Aminocrotonitrile

Product 1

HCID 113785166-Hydroxy-2-methylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
230 °C

Procedure

A solution of (E)-3-amino-but-2-enenitrile (100 g) and propynoic acid methyl ester in DMF (200 ml) was stirred at 25° C. for 2 h and refluxed for additional 1 h. Dowtherm (100 ml) was added and the temperature was raised to 230° C. DMF and MeOH were distilled off. The reaction mixture was cooled down, EtOAc (200 ml) was added and the resulting crystals were filtered off and washed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.).

Workup

  1. temperaturerefluxed for additional 1 h
  2. distillationDMF and MeOH were distilled off
  3. temperatureThe reaction mixture was cooled down
  4. additionEtOAc (200 ml) was added
  5. filtrationthe resulting crystals were filtered off
  6. washwashed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.)

Sources & evidence

ORD record
ord-61b9afaa144d4e7699a02c1b23f562a5
Source dataset
uspto-grants-2014_02
Patent number
US08653075B2

Reaction notes

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