Hydrochloric Acid → 5-Chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one

HRID 24378노트

반응식

HRID 24378 반응식
[CH:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH:21]([CH3:23])[CH3:22])[C:11]=1[O:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)[CH:7]=O)([CH3:3])[CH3:2].[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[CH2:28]2.N1CCCC1.Cl>C(O)C>[Cl:24][C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[NH:30][C:29](=[O:34])[C:28]2=[CH:7][C:6]1[CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:11]([O:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:10]([CH:21]([CH3:23])[CH3:22])[CH:9]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 31268PyrrolidineHCID 1528015-ChlorooxindoleHCID 225711303,5-Diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde

생성물 1

HCID 537278155-Chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one수율 10.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of 3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzaldehyde (0.4 g, 1.26 mmol), 5-chloro-2-oxindole (0.21 g, 1.26 mmol) and pyrrolidine (0.5 ml, 6.3 mmol) in ethanol (2 ml) was held in sealed tube at 100° C. for 12 hours. The mixture was then poured into 1N hydrochloric acid (100 ml) and the solid which remained were filtered and washed with more water (50 ml). The solid was then dissolved in ethyl acetate (200 ml), the solution dried over magnesium sulfate, filtered and then concentrated. The solid which remained was chromatographed (silica, 4/4/1 dichloromethane/hexanes/methanol) to give 60 mg (10%) of 5-chloro-3-[3,5-diisopropyl-4-(2-morpholin-4-ylethoxy)-benzylidene]-1,3-dihydroindol-2-one as a brownish-orange solid.

후처리

  1. filtrationthe solid which remained were filtered
  2. washwashed with more water (50 ml)
  3. dissolutionThe solid was then dissolved in ethyl acetate (200 ml)
  4. dry with materialthe solution dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe solid which remained was chromatographed (silica, 4/4/1 dichloromethane/hexanes/methanol)

출처 및 근거

ORD 기록
ord-219fccfcec6a46d6a15fe396ab23824d
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855730B2

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