Sodium Hydroxide → 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

HRID 2391972Notes

Reaction equation

HRID 2391972 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([O:9]C)=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=[O:8])=[CH:4][C:3]=1[C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57826577Methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylate

Product 1

HCID 578263895-chloro-4-(1-methyl-1H-pyrazol-5-yl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (0.30 g, 1.17 mmole) in THF (10 mL) and MeOH (10 mL) was added 6N NaOH (5 mL). The reaction solution was heated to 50° C. for 2 hrs. The reaction solution was concentrated under vacuum, made acidic (pH ˜2) with 3N HCl, and extracted with DCM. The organic solution was dried (Na2SO4) and concentrated to a solid (0.22 g) which was used without further purification. LC-MS (ES) m/z=243 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated under vacuum
  2. extractionextracted with DCM
  3. dry with materialThe organic solution was dried (Na2SO4)
  4. concentrationconcentrated to a solid (0.22 g) which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-fe1d0fe40d03431a94ba4b85b28fc558
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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