Dimethyl acetylenedicarboxylate → Dimethyl 5-hydroxypyrazolo[1,5-c]quinazoline-1,2-dicarboxylate

HRID 1448170Notes

Reaction equation

HRID 1448170 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][O:14][C:15]([C:17]#[C:18][C:19]([O:21][CH3:22])=[O:20])=[O:16]>C1C=CC=CC=1>[O:12]=[C:4]1[N:1]2[N:2]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([C:15]([O:14][CH3:13])=[O: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 12980Dimethyl acetylenedicarboxylateHCID 136455454(3Z)-3-diazo-1H-indol-2-one

Product 1

HCID 135401800Dimethyl 5-hydroxypyrazolo[1,5-c]quinazoline-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 4.8 g (0.03 mole) of 3-diazooxindole in 150 ml of warm (45°) benzene is treated with 5.10 g (0.036 mole) of dimethylacetylene dicarboxylate. After stirring for 6 hours at 45°, an additional 0.426 g (0.003 mole) of ester is added and reaction continued overnight.

Workup

  1. customreaction continued overnight

Sources & evidence

ORD record
ord-8cfb9ffcc81b455b85c98a729c876ea3
Source dataset
uspto-grants-1979_12
Patent number
US04179561

Reaction notes

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