Methanol → methyl 1H-indazole-3-carboxylate

HRID 1523716Notes

Reaction equation

HRID 1523716 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.S(Cl)(Cl)=O.[CH3:17]O>>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:17])=[O:11])=[N:2]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 657476methyl 1H-indazole-3-carboxylateYield 92%

Procedure

To a stirred solution of indazole-3-carboxylic acid (80.5 grams, 0.497 mmol, obtained in above step) in methanol (2 L) cooled at 0° C. was added thionyl chloride (120 mL, 1.59 mmol) over a period of 1 hour. The reaction temperature was gradually raised and the reaction mixture was refluxed for 5 hours. The volatiles were removed and the crude mass was diluted with dichloromethane, washed with aqueous sodium bicarbonate, dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure to obtain the title compound (80.2 grams).

Workup

  1. temperatureThe reaction temperature was gradually raised
  2. temperaturethe reaction mixture was refluxed for 5 hours
  3. customThe volatiles were removed
  4. additionthe crude mass was diluted with dichloromethane
  5. washwashed with aqueous sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulphate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-186c507b3ae94133bdb2d936c42c4f1e
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

Loading…