Sodium Hydroxide → HCID 58110193, compound

HRID 238278Notes

Reaction equation

HRID 238278 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][NH:13][CH:14]=2)[S:7][CH:6]=1)=[O:4].[OH-].[Na+]>CO>[NH:12]1[CH:11]=[C:10]([C:8]2[S:7][CH:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:9]=2)[CH:14]=[N:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58110358methyl 5-(1H-pyrazol-4-yl)thiophene-3-carboxylate

Product 1

HCID 58110193HCID 58110193, compoundYield 68.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-(1H-Pyrazol-4-yl)-thiophene-3-carboxylic acid methyl ester (2.8 g, 13.3 mmol) was dissolved in a mixture of methanol (18 mL) and a solution of aqueous sodium hydroxide (1 N, 18 mL) and the mixture stirred at 50° C. for 1.5 hours. The mixture was concentrated under vacuum and acidified with aqueous hydrochloric acid (1N). The resulting precipitate was isolated by filtration and washed with water before drying under vacuum to give the title compound as a white solid (1.77 g). LCMS m/z 195.1 [M+H]+. R.T.=3.23 min (Analytical Method 4). 1H NMR (400 MHz, d6-DMSO): δ 8.1 (s, 1H), 8.0 (m, 2H), 7.45 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. custombefore drying under vacuum

Sources & evidence

ORD record
ord-f0015b981396470ca9ca90688886efa0
Source dataset
uspto-grants-2014_02
Patent number
US08642621B2

Reaction notes

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