Potassium Hydroxide → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-carbamoyl-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369072ノート

反応式

HRID 1369072 の反応式
[CH2:1]([N:3]([CH2:33][CH3:34])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:20])([F:19])[F:18])[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:2].[OH-:35].[K+]>C(O)(C)(C)C>[CH2:33]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:17]([F:18])([F:20])[F:19])[CH:11]=[C:12]([C:15](=[O:35])[NH2:16])[CH:13]=2)[C:8]([OH:31])([C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[C:7]1=[O:32])[CH3:34]

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 109616481-(2-Diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole

生成物 1

HCID 111241841-(2-Diethylaminoethyl)-4-trifluoromethyl-6-carbamoyl-3-hydroxy-3-(2-naphthyl)oxindole収率 103%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

反応条件

温度
50 °C

実験手順

To a solution of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-cyano-3-hydroxy-3-(2-naphthyl)oxindole of Example 55 (185 mg, 0.396 mmol) in t-butanol (8 mL) was added powdered KOH (ca. 1 g) at 50° C. The mixture was stirred for 1 h at 50° C. and passed through a celite pad. The celite was washed with THF and the filtrate was concentrated. The residue was dispersed between water and ethyl acetate and the organic layer was separated. The organic layer was dried over MgSO4 and concentrated to give the title compound (198 mg, quant.). The hydrochloride of the title compound was obtained by treating with 4 N HCl in dioxane followed by concentration to dryness.

後処理

  1. washThe celite was washed with THF
  2. concentrationthe filtrate was concentrated
  3. additionThe residue was dispersed between water and ethyl acetate
  4. customthe organic layer was separated
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-34f43ebae4f749628982cb84de309431
出典データセット
uspto-grants-2003_06
特許番号
US06576656B1

反応ノート

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