Hydrochloric Acid → methyl 6-bromo-1H-indazole-4-carboxylate

HRID 38851Notes

Reaction equation

HRID 38851 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([C:12]([OH:14])=[O:13])[C:6]2[CH:7]=[N:8][NH:9][C:10]=2[CH:11]=1.[CH3:15]O>>[Br:2][C:3]1[CH:4]=[C:5]([C:12]([O:14][CH3:15])=[O:13])[C:6]2[CH:7]=[N:8][NH:9][C:10]=2[CH:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 247288386-Bromo-1H-indazole-4-carboxylic acid

Product 1

HCID 24728062methyl 6-bromo-1H-indazole-4-carboxylate

Conditions

Temperature
70 °C

Procedure

Concentrated hydrochloric acid (46.9 ml, 1543 mmol) was added to a stirred suspension of 6-bromo-1H-indazole-4-carboxylic acid (4.65 g, 19.29 mmol, available from Sinova) in methanol (100 ml) and the reaction mixture was heated to 70° C. for 18 h. The reaction mixture was allowed to cool to RT resulting in the precipitation of a solid. The mixture was cooled in ice and the yellow precipitate filtered off and washed with methanol to give the title compound as a yellow solid (2.54 g).

Workup

  1. temperatureto cool to RT
  2. customresulting in the precipitation of a solid
  3. temperatureThe mixture was cooled in ice
  4. filtrationthe yellow precipitate filtered off
  5. washwashed with methanol

Sources & evidence

ORD record
ord-0971d37fb8834f33a644638bca9eada6
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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