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

HRID 2281898노트

반응식

HRID 2281898 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8d6e753db4ba4e80bdade6eaa61d8795
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139587B2

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