Propynamide → 5,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carboxamide

HRID 614545

Reaction equation

HRID 614545 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]([NH2:17])(=[O:16])[C:14]#[CH:15]>C1C=CC=CC=1>[O:12]=[C:4]1[N:1]2[N:2]=[C:14]([C:13]([NH2:17])=[O:16])[CH:15]=[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 101445PropynamideHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 1357356155,6-Dihydro-5-oxopyrazolo[1,5-c]quinazoline-2-carboxamideYield 13.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4.8 g (0.03 mole) of 3-diazooxindole and 2.4 g (0.035 mole) of the propiolamide are taken up in benzene (250 ml) and refluxed overnight under a stream of nitrogen. The light tan precipitates that form are filtered off and dried in a vacuum oven for 4 hours. Yield: 4.4 g. Additional refluxing of the filtrate gives 900 mg of product. Total yield: 5.3 g (77.4%).

Workup

  1. temperaturerefluxed overnight under a stream of nitrogen
  2. customThe light tan precipitates that form
  3. filtrationare filtered off
  4. customdried in a vacuum oven for 4 hours
  5. temperatureAdditional refluxing of the filtrate

Sources & evidence

ORD record
ord-8f14655529db4b009c8a3304b7cd41c5
Source dataset
uspto-grants-1979_03
Patent number
US04145420

Linked notes

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