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

HRID 1582779Notes

Reaction equation

HRID 1582779 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6c366f41bcfc4926aa4434c87cb30cb5
Source dataset
uspto-grants-2004_05
Patent number
US06737547B1

Reaction notes

Loading…