Acetic Anhydride → HCID 13340163, compound

HRID 1249626Notes

Reaction equation

HRID 1249626 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:26])=[N+:7]([O-])[C:8]([CH:11]([O:21][C:22](=[O:24])[CH3:23])[CH2:12][N:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14](=[O:16])[CH3:15])=[CH:9][CH:10]=1)(=[O:3])[CH3:2].[C:27]([O:30]C(=O)C)(=[O:29])[CH3:28].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:1]([O:4][C:5]1[C:6]([CH2:26][O:30][C:27](=[O:29])[CH3:28])=[N:7][C:8]([CH:11]([O:21][C:22](=[O:24])[CH3:23])[CH2:12][N:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:14](=[O:16])[CH3:15])=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 13340162HCID 13340162, compound

Product 1

HCID 13340163HCID 13340163, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1.0 g. (0.0027 mole) of 3-acetoxy-2-methyl-6-[1-acetoxy-2-(N-tert-butylacetamido)ethyl]-pyridine N-oxide in 10 ml. of acetic anhydride was heated at the reflux temperature for 2.5 hours, then was allowed to cool to room temperature and stirred at this temperature overnight. The reaction mixture was poured into a two phase mixture of ethyl acetate and aqueous sodium bicarbonate and stirred for 1 hour. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered and evaporated to dryness in vacuo to give a brown oil which was purified by column chromatography on silica gel with ether as the eluant to give 300 mg. (27%) of the desired product; m.p. 60°-64° C.

Workup

  1. stirringstirred for 1 hour
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo
  6. customto give a brown oil which
  7. customwas purified by column chromatography on silica gel with ether as the eluant
  8. customto give 300 mg

Sources & evidence

ORD record
ord-f9a8c63764514bde84c278cf8c105d37
Source dataset
uspto-grants-1986_12
Patent number
US04632992

Reaction notes

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