Methanol → 5-(1-methyl-1H-pyrazol-3-yl)-thiophene-3-carboxylic acid

HRID 1914565Notes

Reaction equation

HRID 1914565 reaction equation
C[O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[N:11](C)[N:12]=[CH:13][CH:14]=2)[S:7][CH:6]=1)=[O:4].[OH-].[Na+].[CH3:18]O>>[CH3:18][N:12]1[CH:13]=[CH:14][C:10]([C:8]2[S:7][CH:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:9]=2)=[N:11]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 581103165-(2-methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid methyl ester

Product 1

HCID 581102665-(1-methyl-1H-pyrazol-3-yl)-thiophene-3-carboxylic acid

Procedure

5-(2-Methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid methyl ester (0.076 g, 0.34 mmol) was suspended in methanol (0.75 mL) then sodium hydroxide (1 M, 0.41 mL) was added and the mixture stirred for 1.5 hours. A further amount of sodium hydroxide (1 M, 0.41 mL) was added and the mixture stirred overnight. The solution was evaporated, the residue was taken up in HCl (1 N, 1.0 mL) and the resultant precipitate was collected by filtration, washed with water and dried to afford 5-(1-methyl-1H-pyrazol-3-yl)-thiophene-3-carboxylic acid as a grey solid (0.042 g).

Workup

  1. stirringthe mixture stirred overnight
  2. customThe solution was evaporated
  3. filtrationthe resultant precipitate was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4faa2c116c074e83904e5878f1862767
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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