Sodium Hydroxide → HCID 21183696, compound

HRID 1385087Notes

Reaction equation

HRID 1385087 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[CH:14]1([N:11]2[C:12]3[C:8](=[CH:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:13]=3)[CH:9]=[N:10]2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53984079HCID 53984079, compound

Product 1

HCID 21183696HCID 21183696, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3.93 g (16.1 mmol, 1.0 equiv) of 1-cyclopentyl-1H-indazole-6-carboxylic acid methyl ester, 100 mL CH3OH and 50 mL 1N NaOH was heated to reflux for 30 minutes. The reaction mixture was cooled to room temperature, and most of the CH2OH removed on a rotary evaporator. The residue was diluted with 325 mL H2O and acidified to pH=1 with 2N HCl. After stirring 5 minutes, the mixture was filtered, and the solid washed 2×H2O and dried overnight to give 3.42 g (92%) of a yellow powder: mp 172-175° C.; Anal. calcd for C13H14N2O2: C, 67.79; H, 6.13; N, 12.16. Found: C, 67.62; H 5.82; N, 12.19.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. custommost of the CH2OH removed on a rotary evaporator
  4. additionThe residue was diluted with 325 mL H2O
  5. filtrationthe mixture was filtered
  6. washthe solid washed 2×H2O
  7. customdried overnight

Sources & evidence

ORD record
ord-1745ce1fab344d0d98f7766d468ce290
Source dataset
uspto-grants-2001_07
Patent number
US06262040B1

Reaction notes

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