Hydrochloric Acid → 1-butyl-1H-indazole-6-carboxylic acid

HRID 348956

Reaction equation

HRID 348956 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16]C)=[O:15])[CH:12]=2)[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4].C(=O)(O)[O-].[Na+].[OH-].[Na+].Cl>CO>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([OH:16])=[O:15])[CH:12]=2)[CH:7]=[N:6]1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 21086132Methyl 1-butyl-1H-indazole-6-carboxylate

Product 1

HCID 210851661-butyl-1H-indazole-6-carboxylic acidYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of methyl 1-butyl-1H-indazole-6-carboxylate (0.356 g) in methanol (10 mL) was added saturated sodium bicarbonate (5 mL). The mixture was heated at 60° C. for 2 h at which time 1N NaOH (5 mL) was added and the mixture heated to 80° C. for 18 h. The mixture was cooled to room temperature, poured into 1N HCl (50 mL), and extracted with ethyl acetate. The ethyl acetate extract dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give 0.310 g of the title compound: 1H NMR (CDCl3) δ 0.964, 1.96, 4.48, 7.81, 7.89, 8.29, 8.46.

Workup

  1. additionwas added
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd35bc61de74439da8dc953edf137c9a
Source dataset
uspto-grants-2007_02
Patent number
US07176242B2

Linked notes

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