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

HRID 1369072노트

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HRID 1369072 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6386tert-Butanol용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-34f43ebae4f749628982cb84de309431
출처 데이터셋
uspto-grants-2003_06
특허 번호
US06576656B1

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