Methyl propiolate → 6-Hydroxy-2-methylnicotinonitrile

HRID 1422403Notes

Reaction equation

HRID 1422403 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

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 rised 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. customwas rised to 230° C
  3. distillationDMF and MeOH were distilled off
  4. temperatureThe reaction mixture was cooled down
  5. additionEtOAc (200 ml) was added
  6. filtrationthe resulting crystals were filtered off
  7. washwashed with EtOAc and ether affording the title compound (44.8 g, FP>250° C.)

Sources & evidence

ORD record
ord-419c479ac24b45acafa306f3d3b45ef9
Source dataset
uspto-grants-2015_01
Patent number
USRE045323E1

Reaction notes

Loading…