Sodium Hydroxide → 2-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

HRID 8233Notes

Reaction equation

HRID 8233 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[N:12]=2)=[N:9][N:8]2[CH2:18][CH2:19][CH2:20][C:7]=12)=[O:5])C.[OH-].[Na+]>C(O)C>[CH3:17][C:13]1[N:12]=[C:11]([C:10]2[C:6]([C:4]([OH:5])=[O:3])=[C:7]3[CH2:20][CH2:19][CH2:18][N:8]3[N:9]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 693657412-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid ethyl ester

Product 1

HCID 219925742-(6-methylpyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid ethyl ester (1.6 g, 5.9 mmol) and 2 N sodium hydroxide (6 mL, 29 mmol) in absolute ethanol (50 mL) is refluxed for 5 h. The mixture is cooled to room temperature and concentrated in vacuo. The residue is suspended in water and acidified to pH 5 with 1 N hydrochloric acid. The aqueous solution is extracted three times with dichloromethane. The organic extracts are combined, dried (sodium sulfate), filtered, and concentrated in vacuo to yield the title compound, 1.4 g (97%), as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous solution is extracted three times with dichloromethane
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-096d773aff6c4128951312bff972383e
Source dataset
uspto-grants-2006_08
Patent number
US07087626B2

Reaction notes

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