Lithium Hydroxide → 4-(Quinoline-8-sulfonamido)benzoic acid

HRID 1478947

반응식

HRID 1478947 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([O:21]CC)=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:11]([NH:14][C:15]2[CH:25]=[CH:24][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 1357549Ethyl 4-(quinoline-8-sulfonamido)benzoate

생성물 1

HCID 7766454-(Quinoline-8-sulfonamido)benzoic acid수율 95.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
80 °C

실험 절차

To a solution of sulfonamide VII (34 gm, 95.5 mmol) in THF and water (1:1), LiOH (20 gm, 47.66 mmol) was added and the resulting mixture was allowed to stir at 80° C. overnight. After completion of reaction, the crude mixture was washed with EtOAc. The aqueous layer was acidified with citric acid and filtered. Thus obtained solid was washed with Et2O and azeotroped by toluene, under reduced pressure to afford acid VIII (30 gm, 95.8% yield) which was taken forward for the next step without further purification.

후처리

  1. customAfter completion of reaction
  2. washthe crude mixture was washed with EtOAc
  3. filtrationfiltered
  4. washThus obtained solid was washed with Et2O
  5. customazeotroped by toluene, under reduced pressure

출처 및 근거

ORD 기록
ord-342747cd99974e41826eaff6ece488fe
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09404081B2

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