Sulfuric Acid → 5-Acetylfuro(2,3-c)pyridine

HRID 1251565Notes

Reaction equation

HRID 1251565 reaction equation
[O:1]=[C:2]([C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][O:15][C:12]2=[CH:13][N:14]=1)[CH2:3]C(OCC)=O.S(=O)(=O)(O)O.[OH-].[Na+]>C1(C)C=CC=CC=1>[C:2]([C:9]1[CH:10]=[C:11]2[CH:17]=[CH:16][O:15][C:12]2=[CH:13][N:14]=1)(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 18324176Ethyl beta-oxo-5-furo[2,3-c]pyridinepropionate

Product 1

HCID 97939025-Acetylfuro(2,3-c)pyridineYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl β-oxo-5-furo[2,3-c]pyridinepropionate(1.17 g, 15 5.0 mmol) was dissolved in 20 mL of toluene, and 1.5 mL (7.5 mmol) of 10 N sulfuric acid was added at room temperature with stirring. After addition, the reaction mixture was heated to 80° C., and a reaction was carried out for 6 hours with stirring. The solution was then cooled to room temperature and neutralized with 12 mL of 5% sodium hydroxide aqueous solution. The organic layer was separated, the aqueous layer was extracted twice with 5 mL of methylene chloride, and the combined organic layer was dried with anhydrous magnesium sulfate and then concentrated in a rotary evaporator. The resulting solids were recrystallized from a mixed solvent of toluene-hexane, giving 580 mg of 5-acetylfuro[2,3-c]pyridine in a purity of 99% by HPLC (72% yield).

Workup

  1. additionAfter addition
  2. stirringwith stirring
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with 5 mL of methylene chloride
  5. dry with materialthe combined organic layer was dried with anhydrous magnesium sulfate
  6. concentrationconcentrated in a rotary evaporator
  7. customThe resulting solids were recrystallized from a mixed solvent of toluene-hexane

Sources & evidence

ORD record
ord-8cf036c9f3b74119a09a17950e2ec080
Source dataset
uspto-grants-2002_01
Patent number
US06342606B2

Reaction notes

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