Water → Methyl-5-oxo-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxylate

HRID 1927291Notes

Reaction equation

HRID 1927291 reaction equation
Cl.[NH:2]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)[NH2:3].[CH2:13]([O:15][CH:16]=[C:17]([C:20]#N)[C:18]#[N:19])C.[O-:22]CC.[Na+].O>CCO>[CH3:13][O:15][C:16]([C:17]1[CH:20]=[N:3][N:2]2[C:4]3[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:6](=[O:8])[NH:19][C:18]=12)=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 671522-(Ethoxymethylene)propanedinitrileHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 2723922Sodium ethoxide

Product 1

HCID 136389266Methyl-5-oxo-4,5-dihydropyrazolo[1,5-a]quinazoline-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-hydrazinylbenzoic acid hydrochloride (10 g, 53 mmol), 2-(ethoxymethylene)malononitrile (6.5 g, 53.2 mmol) and sodium ethoxide (4.85 g, 257 mmol) in EtOH (100 mL) was refluxed overnight then cooled to ambient temperature. Water was added and the mixture was stirred at ambient temperature for 1 h then filtered. The solid was washed with H2O, EtOH and Et2O then dried.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationthen filtered
  3. washThe solid was washed with H2O, EtOH and Et2O
  4. customthen dried

Sources & evidence

ORD record
ord-391fcd7d3502490dbc94dbabb9bbe8a3
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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