Propargyl alcohol → Pirquinozol

HRID 616944Notes

Reaction equation

HRID 616944 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 55.3%

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 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
  5. customto give
  6. custom2.0 of product (75% direct yield)
  7. customRecrystallization from methanol

Sources & evidence

ORD record
ord-897bc27b97114e3b8275c541eba0b850
Source dataset
uspto-grants-1978_02
Patent number
US04076818

Reaction notes

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