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

HRID 1890272Notes

Reaction equation

HRID 1890272 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([C:19]([O:21]C)=[O:20])=[C:12]3[CH2:17][CH2:16][CH:15]([CH3:18])[N:13]3[N:14]=2)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([C:19]([OH:21])=[O:20])=[C:12]3[CH2:17][CH2:16][CH:15]([CH3:18])[N:13]3[N:14]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67437517methyl 2-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate

Product 1

HCID 674367222-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

36.8 ml (73.6 mmol) of a 2 M aqueous NaOH solution are added to a solution of 7.0 g (25.5 mmol) of methyl 2-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate in 50 ml of methanol, and the mixture is stirred for 3 h. The reaction mixture is concentrated under reduced pressure, ethyl acetate/1 M hydrochloric acid is added, the organic phase is separated off and the aqueous phase is extracted with 3×100 ml of ethyl acetate. The combined organic phases are dried over Na2SO4 and freed from the solvent under reduced pressure. The 2-(4-fluorophenyl)-6-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid obtained (5.9 g) is reacted further without further purification.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, ethyl acetate/1 M hydrochloric acid
  2. additionis added
  3. customthe organic phase is separated off
  4. extractionthe aqueous phase is extracted with 3×100 ml of ethyl acetate
  5. dry with materialThe combined organic phases are dried over Na2SO4

Sources & evidence

ORD record
ord-de2cd1bf2a4d4c9ba004b9bbc2d7f507
Source dataset
uspto-grants-2013_08
Patent number
US08507472B2

Reaction notes

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