Sodium Hydroxide → HCID 178524797, compound

HRID 2271099Notes

Reaction equation

HRID 2271099 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[C:8]([C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=2)=[CH:9][NH:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>>[O:21]=[C:12]1[C:8]2=[CH:9][NH:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]2=[N:14][N:13]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 178469890HCID 178469890, compound

Product 1

HCID 178524797HCID 178524797, compoundYield 76%

Procedure

A mixture of 3,5-dihydro-3-oxo-2-phenyl-2H-pyrazolo[4,3-c]pyridine-7-carboxylic acid ethyl ester (0.9522 g, 3.36 mmol) in 1N aqueous NaOH (16 ml, 16.0 mmol) was stirred at room temperature for 3.25 h. The mixture was filtered, and the filtrate was neutralised to pH 5 by the addition of 5N aqueous HCl (3 ml). The resulting solid was collected by filtration, washed with water, then hexane, and dried under vacuum at 70° C. to leave 0.6498 g (76%) of the title compound as an orange solid; mp 287-302° C.; 1H NMR (360 MHz, DMSO-d6) δ7.18 (1H, t, J 7.4 Hz), 7.44 (2H, t, J 7.5 Hz), 8.12 (1H, s), 8.17 (2H, d, J 7.6 Hz), 8.56 (1H, s), 12.66 (1H, br s); MS (ES+) m/z 256 [MH]+. Anal. found: C, 59.81; H, 3.49; N, 16.27. C13H9N3O3.0.3H2O requires: C, 59.91; H, 3.71; N, 16.12%.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was neutralised to pH 5 by the addition of 5N aqueous HCl (3 ml)
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water
  5. dry with materialhexane, and dried under vacuum at 70° C.

Sources & evidence

ORD record
ord-bdafd801e0484b1fbe45bbf4136b77a0
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

Loading…