Lithium Hydroxide → 3-cyano-1H-indazole-5-carboxylic acid

HRID 2281898Notes

Reaction equation

HRID 2281898 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14]C)=[O:13])[CH:10]=2)[NH:5][N:4]=1)#[N:2].[OH-].[Li+]>C(O)C.O>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([OH:14])=[O:13])[CH:10]=2)[NH:5][N:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 44632177Methyl 3-cyano-1H-indazole-5-carboxylate

Product 1

HCID 671512173-cyano-1H-indazole-5-carboxylic acidYield 84.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 3-cyano-1H-indazole-5-carboxylate (2.5 g, 12 mmol) in ethanol (40 mL), a solution of lithium hydroxide (1.04 g, 24.9 mmol) in water (15 mL) was added and stirred at ambient temperature for 16 h. The mixture was concentrated and the obtained residue was dissolved in water (25 mL) and washed with ethyl acetate (20 mL). The aqueous layer was acidified with 10% citric acid solution, the obtained precipitate was filtered, washed with 50% ethyl acetate in petroleum ether (2×10 mL) and dried to afford the title compound (1.9 g, 82%) as a brown solid. 1HNMR (DMSO-d6) δ ppm 13.8-12.4 (br, 2H), 8.44 (s, 1H), 8.1 (d, 1H), 7.82 (d, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe obtained residue was dissolved in water (25 mL)
  3. washwashed with ethyl acetate (20 mL)
  4. filtrationthe obtained precipitate was filtered
  5. washwashed with 50% ethyl acetate in petroleum ether (2×10 mL)
  6. customdried

Sources & evidence

ORD record
ord-8d6e753db4ba4e80bdade6eaa61d8795
Source dataset
uspto-grants-2015_09
Patent number
US09139587B2

Reaction notes

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