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

HRID 1927290Notes

Reaction equation

HRID 1927290 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].[C:13](/[C:15](=[CH:21]\OCC)/[C:16]([O:18][CH2:19]C)=[O:17])#[N:14].C([O-])(=O)C.[Na+].O>CN(C=O)C>[CH3:19][O:18][C:16]([C:15]1[CH:21]=[N:3][N:2]2[C:4]3[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:6](=[O:8])[NH:14][C:13]=12)=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 1715183Ethyl 2-cyano-3-ethoxyacrylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-hydrazinylbenzoic acid hydrochloride (1.05 g, 5.57 mmol), (E)-ethyl 2-cyano-3-ethoxyacrylate (0.9 g, 5.32 mmol) and sodium acetate (0.457 g, 5.57 mmol) in DMF (7 mL) was heated to 140° C. for 2 h then cooled. Water (5 mL) 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. temperaturethen cooled
  2. filtrationthen filtered
  3. washThe solid was washed with H2O, EtOH and Et2O
  4. customthen dried

Sources & evidence

ORD record
ord-c64623aae70b4548a6b0f3f527107b67
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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