Propargyl alcohol → Pirquinozol

HRID 1448180Notes

Reaction equation

HRID 1448180 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]>C(OCC)C>[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 alcoholHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 135449340PirquinozolYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.0 g (0.0126 mole) of 3-diazooxindole is dissolved in 22 ml of propargyl alcohol (0.378 mole) and refluxed under nitrogen for 3 hours. The reaction mixture is cooled to room temperature and diluted with 10 volumes of ethyl ether. The solid is filtered, washed with ethyl ether and dried to give 2.0 g of product (75% direct yield). Recrystallization from methanol gives 1.5 g of title compound, m.p. 286°-288° (sl. dec.).

Workup

  1. temperaturerefluxed under nitrogen for 3 hours
  2. filtrationThe solid is filtered
  3. washwashed with ethyl ether
  4. customdried

Sources & evidence

ORD record
ord-55d33510618d4b9cb72e4d6cbf1dcc6a
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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