Butyn-2-one → HCID 135735613, compound

HRID 1448163Notes

Reaction equation

HRID 1448163 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].[CH3:13][C:14](=[O:17])[C:15]#[CH:16]>C1C=CC=CC=1>[C:14]([C:15]1[CH:16]=[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)(=[O:17])[CH3:13]

Participants

4

Reactant 2

HCID 15018Butyn-2-oneHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 135735613HCID 135735613, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 19.0 g (0.119 mole) of 3-diazooxindole and 10 g (0.147 mole) of 3-butyn-2-one in 800 ml of benzene is refluxed overnight. The reaction mixture is cooled to room temperature and the product filtered off (23.1 g). Recrystallization from methanol/chloroform gives 18.0 g of product with melting point 296°-229° (d). Further recrystallization from glacial acetic acid gives 14.2 g of pure product melting at 306°-308° (d).

Workup

  1. filtrationthe product filtered off (23.1 g)
  2. customRecrystallization from methanol/chloroform

Sources & evidence

ORD record
ord-a704f6cce2f849c7870eb65f50852a2f
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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