Hydrochloric Acid → HCID 66723847, compound

HRID 928451Notes

Reaction equation

HRID 928451 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([O:19]CC)=[O:18])[CH:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:22].[OH-].[Na+].Cl>O1CCOCC1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH2:11][N:12]3[CH:16]=[C:15]([C:17]([OH:19])=[O:18])[CH:14]=[N:13]3)=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH3:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66723638HCID 66723638, compound

Product 1

HCID 66723847HCID 66723847, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Ethyl 1-((1,2-dimethyl-1H-indol-5-yl)methyl)-1H-pyrazole-4-carboxylate (88%, 122 mg, 0.361 mmol) and 2 N NaOH (0.9 ml, 1.8 mmol) in dioxane (1 ml) was stirred at rt for 16 hours. The reaction mixture was acidified with 1 N HCl to pH 2 and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum to afford crude 1-((1,2-dimethyl-1H-indol-5-yl)methyl)-1H-pyrazole-4-carboxylic acid.

Workup

  1. extractionextracted with EtOAc (2×)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b6aa099441db442887fac1722c62b30e
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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