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Ammonium formate → 2-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

HRID 2383369
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인쇄 미리보기

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HRID 2383369 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][N:12]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13]2=[O:22])=[CH:6][CH:5]=1.C([O-])=O.[NH4+]>C(O)C.C(OCC)(=O)C.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][N:12]2[C:13](=[O:22])[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]2=[O:21])=[CH:8][CH:9]=1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 2723923Ammonium formate2회HCID 670291452-{2-[4-(2-Hydroxy-ethyl)phenyl]-vinyl}-isoindole-1,3-dione

생성물 1

HCID 591459612-{2-[4-(2-Hydroxy-ethyl)phenyl]-ethyl}-isoindole-1,3-dione

시약·촉매·용매 3

HCID 9942167Palladium hydroxide촉매2회HCID 702Ethanol용매
HCID 8857
Ethyl Acetate
용매

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 2-{2-[4-(2-Hydroxy-ethyl)-phenyl]-vinyl}-isoindole-1,3-dione (Preparation 9, 10 g) in ethanol and ethyl acetate (350 mL each) was added 30% palladium hydroxide on carbon (1.44 g) followed by ammonium formate (21.5 g). The reaction was heated to 80° C. for 4 hours. Additional palladium hydroxide on carbon (1.44 g) and ammonium formate (21.5 g) were added and the reaction was stirred at 80° C. for 18 hours. The reaction was cooled, filtered through a pad of Arbocel® and rinsed with methanol. The solvent was removed under reduced pressure and the resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml). The aqueous layer was separated and extracted with further dichloromethane (2×50 mL). The combined organic layers were dried (sodium sulphate) and the solvent removed in vacuo to give the title compound as an off-white solid, 9.11 g.

후처리

  1. temperatureThe reaction was cooled
  2. filtrationfiltered through a pad of Arbocel®
  3. washrinsed with methanol
  4. customThe solvent was removed under reduced pressure
  5. customthe resulting white solid was partitioned between dichloromethane (200 ml) and water (100 ml)
  6. customThe aqueous layer was separated
  7. extractionextracted with further dichloromethane (2×50 mL)
  8. dry with materialThe combined organic layers were dried (sodium sulphate)
  9. customthe solvent removed in vacuo

출처 및 근거

ORD 기록
ord-c06ddca49df84140a8c9b8ce0816efed
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08263623B2

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