Propargyl alcohol → Pirquinozol

HRID 1448181Notes

Reaction equation

HRID 1448181 reaction equation
[N+:1](=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])=[N-:2].[CH2:13]([OH:16])[C:14]#[CH:15]>C1C=CC=CC=1>[OH:16][CH2:13][C:14]1[CH:15]=[C:3]2[N:1]([C:4](=[O:12])[NH:5][C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=32)[N:2]=1

Participants

4

Reactant 2

HCID 7859Propargyl alcohol2×HCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 135449340PirquinozolYield 23%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 g (0.03 mole) of 3-diazooxindole is suspended in 500 ml of benzene and 1.96 g (0.033 mole) of propargyl alcohol added. The reaction mixture is refluxed overnight under nitrogen, after which 19.6 g (0.33 mole) of propargyl alcohol is added and the reaction continued under reflux for a total of 48 hours. The tan solid which precipitates is filtered off (1.5 g, 23% yield), m.p. 272°-275° (sl. dec.). Recrystallization from methanol gives crystals of the title compound, m.p. 286°-288° (sl. dec.).

Workup

  1. temperatureThe reaction mixture is refluxed overnight under nitrogen
  2. temperatureunder reflux for a total of 48 hours
  3. customThe tan solid which precipitates
  4. filtrationis filtered off (1.5 g, 23% yield), m.p. 272°-275° (sl. dec.)
  5. customRecrystallization from methanol

Sources & evidence

ORD record
ord-bbcd62cc220b4d7e9fb866509cd54ab2
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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