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Acetic Anhydride → N-1H-Inden-3-ylacetamide

HRID 1582779
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HRID 1582779 반응식
[C:1]1(=[N:10]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>N1C=CC=CC=1>[C:12]([NH:10][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1)(=[O:14])[CH3:13]
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참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 3023232,3-Dihydro-1H-inden-1-one oxime

생성물 1

HCID 10130185N-1H-Inden-3-ylacetamide

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

1-Indanone oxime (7.02 g, 0.048 moles), pyridine (250 ml) and acetic anhydride (170 ml) were stirred and heated under nitrogen at reflux for 16.5 hours. The cooled mixture was evaporated in vacuo and the residue agitated thoroughly with 1N sodium carbonate solution and ether (250 ml each). The liquid was filtered through filter-aid and the black solid treated again with sodium carbonate/ether and filtered. The combined ether extracts and washes were dried (MgSO4) and evaporated to a black-orange oil (8.6 g). This was applied to a column of basic alumina, allowed to stand for 2.5 hours and eluted with ethyl acetate/hexane 1:2 v/v. The appropriated fractions were evaporated to leave a crude solid (3 g). This was recrystallized from ethyl acetate/hexane to give the title product, mp. 139° C., (1.44 g, 17%) with the same IR spectrum as in Example 1.

후처리

  1. temperatureheated under nitrogen
  2. temperatureat reflux for 16.5 hours
  3. customThe cooled mixture was evaporated in vacuo
  4. filtrationThe liquid was filtered
  5. filtrationthrough filter-aid
  6. additionthe black solid treated again with sodium carbonate/ether
  7. filtrationfiltered
  8. dry with materialThe combined ether extracts and washes were dried (MgSO4)
  9. customevaporated to a black-orange oil (8.6 g)
  10. washeluted with ethyl acetate/hexane 1:2 v/v
  11. customThe appropriated fractions were evaporated
  12. customto leave a crude solid (3 g)
  13. customThis was recrystallized from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-6c366f41bcfc4926aa4434c87cb30cb5
출처 데이터셋
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06737547B1

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