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

HRID 1961066Notes

Reaction equation

HRID 1961066 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+].Cl>O1CCCC1.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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 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

Procedure

To a 250 mL round-bottomed flask was added methyl 5-chloro-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxylate (4.4 g, 17.14 mmol) and sodium hydroxide (28.6 ml, 171 mmol) in tetrahydrofuran (THF) (50 ml) and MeOH (50 mL). The reaction solution was stirred at RT for 12 h and then made acidic (pH ˜2) with 2.5 M HCl and extracted with DCM. The organic layer was separated, dried (Na2SO4) and concentrated to an off-white solid (4.2 g, 94%) which was used directly without further purification: LCMS (ES) m/z 243 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated to an off-white solid (4.2 g, 94%) which
  5. customwas used directly without further purification

Sources & evidence

ORD record
ord-d3495dffd58b43649dd50d6908ae94d5
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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