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

HRID 2068630Notes

Reaction equation

HRID 2068630 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-32e54a88148744bd911a5b6c8e111921
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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