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

HRID 1892598ノート

反応式

HRID 1892598 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 671512173-cyano-1H-indazole-5-carboxylic acid収率 84.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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-d) δ ppm 13.8-12.4 (br, 2H), 8.44 (s, 1H), 8.1 (d, 1H), 7.82 (d, 1H).

後処理

  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

出典と根拠

ORDレコード
ord-492e58f3e73241fc9fd04fe5a4127553
出典データセット
uspto-grants-2013_08
特許番号
US08507681B2

反応ノート

読み込み中…