1H-Indazole-6-carboxylic acid, 2,3-dihydro-2-methyl-3-oxo- synthesis
- Product Name:1H-Indazole-6-carboxylic acid, 2,3-dihydro-2-methyl-3-oxo-
- CAS Number:1374258-65-7
- Molecular formula:C9H8N2O3
- Molecular Weight:192.17
1374258-57-7
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Yield:1374258-65-7 55%
Reaction Conditions:
Stage #1: 1-ethyl 6-methyl 2-methyl-3-oxo-2,3-dihydro-1H-indazole-1,6-dicarboxylatewith water;potassium hydroxide in ethanol at 65; for 1.5 h;
Stage #2: with hydrogenchloride in water;
Steps:
33
To a suspension of 1-ethyl 6-methyl 2-methyl-3-oxo-2,3-dihydro-1H-indazole-1,6-dicarboxylate (formed in Step 3 of Intermediate 28) (514 mg, 1.85 mmol) in ethanol (6 mL) was added 1 N aqueous potassium hydroxide (18.5 mL, 18.5 mmol). The reaction was heated to 65° C. for 1.5 hours. The reaction was cooled to room temperature and concentrated to dryness. The residue was taken up in water and acidified with 1 N aqueous hydrochloric acid until a precipitate formed. The solid was collected by filtration and dried under vacuum to give the title compound (196 mg, 55%) as a brown solid. 1H NMR (400 MHz, DMSO-d6, δ): 13.12 (br. s., 1H), 10.61 (br. s., 1H), 7.76 (s, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.60 (dd, J=8.2, 1.2 Hz, 1H), 3.38 (s, 3H).
References:
US2012/108619,2012,A1 Location in patent:Page/Page column 43
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