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

HRID 880931Notes

Reaction equation

HRID 880931 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+]>CO>[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

4

Reactant 2

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

Product 1

HCID 671512173-cyano-1H-indazole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 3-cyano-1H-indazole-5-carboxylate (500 mg, 2.5 mmol) was dissolved in methanol (12 mL) and 2 N aqueous lithium hydroxide (3.7 mL, 7 mmol) was added. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated to remove the methanol and the residue was acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting yellow precipitate was collected by filtration, washed with water, and dried in a vacuum oven to provide the title compound (445 mg, 96%). −ESI (M−H) 186.4; 1H NMR (400 MHz, DMSO-d6, δ): 13.17 (br. s., 1H), 8.42 (s, 1H), 8.05 (dd, J=8.8, 1.6 Hz, 1H), 7.83 (d, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto remove the methanol
  3. filtrationThe resulting yellow precipitate was collected by filtration
  4. washwashed with water
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-281d3ddb65164834ad7d2102943228de
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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