2-Propynenitrile → 5,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carbonitrile

HRID 65680

Reaction equation

HRID 65680 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].[C:13]([C:15]#[CH:16])#[N:14]>C1C=CC=CC=1>[O:12]=[C:4]1[N:1]2[N:2]=[C:15]([C:13]#[N:14])[CH:16]=[C:3]2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5]1

Participants

4

Reactant 2

HCID 140552-PropynenitrileHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 1357356215,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

6.0 g (0.04 mole) of 3-diazooxindole and 2.2 g (0.045 mole) of cyanoacetylene are taken up in benzene (250 ml) and refluxed overnight under N2. The mixture is cooled and the beige-colored precipitates are filtered off. The crude product is dried in a vacuum oven at room temperature for 3 hours. Yield: 5.2 g, m.p. 302°-304°. Percent yield: 65.6.

Workup

  1. temperaturerefluxed overnight under N2
  2. temperatureThe mixture is cooled
  3. customthe beige-colored precipitates
  4. filtrationare filtered off
  5. dry with materialThe crude product is dried in a vacuum oven at room temperature for 3 hours

Sources & evidence

ORD record
ord-17badc783a4f4776bd16b92132f8856e
Source dataset
uspto-grants-1978_12
Patent number
US04128644

Linked notes

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