Hydrochloric Acid → Methyl 1H-indazole-5-carboxylate

HRID 22657Notes

Reaction equation

HRID 22657 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.Cl>CO>[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15][CH3:16])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[N:5]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22591332Methyl 1-acetyl-1H-indazole-5-carboxylate

Product 1

HCID 22260640Methyl 1H-indazole-5-carboxylateYield 96.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 1-acetyl-1H-indazole-5-carboxylate (1.16 g, 5.31 mmol) in methanol (10 mL) is added HCl (10 mL of a 6.0 M aqueous solution). The mixture is stirred at rt overnight. The methanol is removed in vacuo, and the remaining aqueous solution is basified with 30% aqueous NH4OH to pH=8. The resulting precipitate is collected by filtration, washed with water and dried in vacuo to afford 900 mg (96%) of methyl 1H-indazole-5-carboxylate as a light yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 13.4, 8.5, 8.3, 7.9, 7.6, 3.9.

Workup

  1. customThe methanol is removed in vacuo
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6af911d2abcf4e7d9619a0a8a3275476
Source dataset
uspto-grants-2005_02
Patent number
US06849620B2

Reaction notes

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