| Identification | More | [Name]
5-Carboxyindazole hydrochloride | [CAS]
61700-61-6 | [Synonyms]
1H-INDAZOLE-5-CARBOXYLIC ACID
5-(1H)INDAZOLE CARBOXYLIC ACID
5-CARBOXYINDAZOLE HCL
5-CARBOXYINDAZOLE HYDROCHLORIDE
5-INDAZOLECARBOXYLIC ACID
INDAZOLE-5-CARBOXYLIC ACID
1H-Indazole-5-carboxylic acid methyl ester
Indazole-5-carboxylic acid hydrochloride
1H-INDAZOLE-5-CARBOXYLATE | [Molecular Formula]
C8H7ClN2O2 | [MDL Number]
MFCD03426158 | [Molecular Weight]
198.61 | [MOL File]
61700-61-6.mol |
| Chemical Properties | Back Directory | [Melting point ]
>250℃ | [Boiling point ]
443.7±18.0 °C(Predicted) | [density ]
1.506±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [form ]
Spherical Beads | [pka]
4.03±0.30(Predicted) | [color ]
Yellow to amber | [InChI]
1S/C8H6N2O2/c11-8(12)5-1-2-7-6(3-5)4-9-10-7/h1-4H,(H,9,10)(H,11,12) | [InChIKey]
MAVGBUDLHOOROM-UHFFFAOYSA-N | [SMILES]
OC(=O)c1ccc2[nH]ncc2c1 | [CAS DataBase Reference]
61700-61-6(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Uses]
1H-Indazole-5-carboxylic Acid is used as a reactant in the synthesis of azabicyclic aryl amides as α7 nicotinic acetylcholine receptor agonists. | [Synthesis]
General procedure for the synthesis of indazole-5-carboxylic acid hydrochloride from methyl 1H-indazole-5-carboxylate: 1H-indazole-5-carboxylic acid methyl ester (6.5 g, 1.0 eq.) and 200 mL of methanol (MeOH) were added to a stirred 1 L reaction flask, followed by a solution of sodium hydroxide (NaOH, 4.4 g, 3.0 eq.) dissolved in 150 mL of water (H2O). The reaction mixture was heated to reflux for 1 hour. Upon completion of the reaction, the organic solvent was evaporated under reduced pressure. The remaining aqueous phase was washed with ethyl acetate (EtOAc) and then acidified with 3N hydrochloric acid (HCl) to pH=5~6. The precipitate was collected by filtration and washed with deionized water to afford the target product, indazole-5-carboxylic acid hydrochloride, as a yellow solid (6.2 g, 98% yield). | [References]
[1] Patent: WO2013/97773, 2013, A1. Location in patent: Paragraph 0261
[2] Patent: US2012/277224, 2012, A1. Location in patent: Page/Page column 40
[3] Patent: WO2014/66743, 2014, A1. Location in patent: Paragraph 0146
[4] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8219 - 8248 |
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