Pyridine → 3-Acetamidononan-2-one

HRID 27589Notes

Reaction equation

HRID 27589 reaction equation
[NH2:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3]([OH:5])=O.N1C=CC=C[CH:13]=1.[C:18](OC(=O)C)(=[O:20])[CH3:19]>>[C:18]([NH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:3](=[O:5])[CH3:13])(=[O:20])[CH3:19]

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 695222-Aminooctanoic acid

Product 1

HCID 3214653-Acetamidononan-2-one

Procedure

A mixture of 2-amino-1-octanoic acid (I, 200 g, 1.26 mole) in acetic anhydride (960 ml), and pyridine (640 ml) was heated on a boiling water bath for 4 hr. The reaction mixture was evaporated in vacuo, and the residue was partitioned 6-8 times between 5% aqueous solution of NaHCO3 (400 ml) and ether (400 ml). The combined ethereal extracts were dried with anhydrous MgSO4 and evaporated to dryness to give crude 3-acetamidononan-2-one, 154 g (70%).

Workup

  1. temperaturewas heated on a boiling water bath for 4 hr
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was partitioned 6-8 times between 5% aqueous solution of NaHCO3 (400 ml) and ether (400 ml)
  4. dry with materialThe combined ethereal extracts were dried with anhydrous MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ee6da5b7d9a44f08b8ffc5535af0bebd
Source dataset
uspto-grants-1980_09
Patent number
US04221909

Reaction notes

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