Acetic Anhydride → HCID 13340161, compound

HRID 1632829Notes

Reaction equation

HRID 1632829 reaction equation
Cl.Cl.[OH:3][CH:4]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:18])[N:12]=1)[CH2:5][NH:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O:22][CH2:23][CH3:24])(=O)C.[C:25](OC(=O)C)(=[O:27])[CH3:26].[C:32](=[O:35])(O)[O-].[Na+].[CH2:37](N(CC)CC)C>>[C:25]([O:17][C:14]1[C:13]([CH3:18])=[N:12][C:11]([CH:4]([O:3][C:23](=[O:22])[CH3:24])[CH2:5][N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:32](=[O:35])[CH3:37])=[CH:16][CH:15]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 5

HCID 7918Acetic Anhydride2×HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 12397275HCID 12397275, compound

Product 1

HCID 13340161HCID 13340161, compound

Procedure

To a suspension of 2-(1-hydroxy-2-tert-butylaminoethyl)-5-hydroxy-6-methylpyridine dihydrochloride (7.70 g., 0.026 mole) in 300 ml. of ethyl acetate and 7.7 ml. of triethylamine, 10.8 ml. of acetic anhydride was added and the solution was heated at the reflux temperature for 30 hours. An additional 5 ml. of acetic anhydride was added to the reaction mixture and heating was continued for 24 hours, then allowed to cool to room temperature. The reaction mixture was poured into aqueous sodium bicarbonate solution (100 g. NaHCO3 in 700 ml. H2O) and the resulting mixture was stirred for 1 hour. The ethyl acetate layer was separated, washed with aqueous sodium bicarbonate, then water and dried over magnesium sulfate. Evaporation of the dried ethyl acetate solution in vacuo gave 3-acetoxy-2-methyl-6-[1-acetoxy-2-(N-tert-butylacetamido)ethyl]pyridine, the product 6.0 g. (66%); m.p. 124.5°-127.5° C.

Workup

  1. temperaturethe solution was heated at the reflux temperature for 30 hours
  2. temperatureheating
  3. customThe ethyl acetate layer was separated
  4. washwashed with aqueous sodium bicarbonate
  5. dry with materialwater and dried over magnesium sulfate
  6. customEvaporation of the dried ethyl acetate solution in vacuo

Sources & evidence

ORD record
ord-3801cfd6634a4cacb30bb122f032cf55
Source dataset
uspto-grants-1984_10
Patent number
US04477671

Reaction notes

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