Sodium Hydroxide → 5-oxo-1H,5H-pyrazolo[1,5-a]quinazoline-3-carboxylic acid

HRID 1927289Notes

Reaction equation

HRID 1927289 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]CC)=[O:17])#[N:14].C([O-])(=O)C.[Na+].[OH-].[Na+]>CN(C=O)C.O>[O:8]=[C:6]1[C:5]2[C:4](=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:2]2[N:3]=[CH:21][C:15]([C:16]([OH:18])=[O:17])=[C:13]2[NH:14]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 104169Benzoic acid, 2-hydrazinyl-, hydrochloride (1:1)HCID 517045Sodium AcetateHCID 1715183Ethyl 2-cyano-3-ethoxyacrylate

Product 1

HCID 1354730455-oxo-1H,5H-pyrazolo[1,5-a]quinazoline-3-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 rt for 1 h then filtered. The solid was washed with H2O, EtOH and Et2O then dried. The solid was dissolved in EtOH (10 mL), treated with a 1M solution of sodium hydroxide (23 mL, 23 mmol) and the mixture was heated at 80° C. for 18 hr. The mixture was filtered hot then cooled and acidified with acetic acid and 10% HCl. The precipitated product was filtered, washed with H2O and Et2O, dried well and used without any further purification.

Workup

  1. temperaturethen cooled
  2. filtrationthen filtered
  3. washThe solid was washed with H2O, EtOH and Et2O
  4. customthen dried
  5. dissolutionThe solid was dissolved in EtOH (10 mL)
  6. temperaturethe mixture was heated at 80° C. for 18 hr
  7. filtrationThe mixture was filtered hot
  8. temperaturethen cooled
  9. filtrationThe precipitated product was filtered
  10. washwashed with H2O and Et2O
  11. customdried well
  12. customused without any further purification

Sources & evidence

ORD record
ord-b70e400a1452480db80a12716f69c54d
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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