Acetic Anhydride → HCID 67414838, compound

HRID 2212815Notes

Reaction equation

HRID 2212815 reaction equation
[N:1]1[C:9]2[C:8](=O)[C:7](=[N:11]O)[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(O)(=O)C.[Pd]>[N:1]1[C:9]2[CH2:8][CH:7]([NH:11][C:13](=[O:15])[CH3:14])[CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 859288435H-Cyclopenta[b]pyridine-6,7-dione, 6-oxime

Product 1

HCID 67414838HCID 67414838, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

18 g (0.11 mol) of the compound of step c were dissolved in 500 ml of acetic acid and 500 ml of acetic acid anhydride and hydrogenated for 20 h at a pressure of 2 bar over 5 g of palladium on barium sulfate. The reaction mixture was filtered and evaporated. The residue was dissolved in 1000 ml of ethanol, treated with 10.8 ml of perchloric acid and hydrogenated for 10 h at 50° C. and a pressure of 3.5 bar over 5 g of palladium on charcoal (10%). The resulting mixture was evaporated, the residue taken up in dilute NaOH solution and extracted with ethyl acetate. Evaporation of the combined organic phases and subsequent chromatography of the residue yielded racemic N-(6,7-dihydro-5H-[1]pyrindin-6-yl)acetamide.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated
  3. dissolutionThe residue was dissolved in 1000 ml of ethanol
  4. additiontreated with 10.8 ml of perchloric acid and hydrogenated for 10 h at 50° C.
  5. customThe resulting mixture was evaporated
  6. extractionextracted with ethyl acetate
  7. customEvaporation of the combined organic phases and subsequent chromatography of the residue

Sources & evidence

ORD record
ord-c296e491c9d34ae4b96f9475c307af97
Source dataset
uspto-grants-2006_09
Patent number
US07105513B2

Reaction notes

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