Lithium Hydroxide → 3-cyano-1H-indazole-6-carboxylic acid
Reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14]C)=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1)#[N:2].[OH-].[Li+]>CO.O1CCCC1>[C:1]([C:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([OH:14])=[O:13])=[CH:9][CH:10]=2)[NH:5][N:4]=1)#[N:2]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 50 °C
Procedure
To a solution of methyl 3-cyano-1H-indazole-6-carboxylate (1.47 g, 7.31 mmol) in methanol (36 mL) and tetrahydrofuran (20 mL) was added 2 N aqueous lithium hydroxide (16 mL, 32 mmol). The reaction was heated to 50° C. for 72 hours. The reaction was cooled to room temperature and concentrated. The residue was diluted with water and the pH was adjusted to 4 with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered off, rinsed with water, and dried under vacuum to provide the title compound (500 mg, 37%) as a tan solid. +ESI (M+H) 188.2.
Workup
- temperatureThe reaction was cooled to room temperature
- concentrationconcentrated
- additionThe residue was diluted with water
- filtrationThe resulting precipitate was filtered off
- washrinsed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-432b744c585643be9ac736549c854d94
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181252B2
Reaction notes
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