Acetone → Furo[2,3-b]pyridine-5,6-dicarboxylic acid

HRID 2073980Notes

Reaction equation

HRID 2073980 reaction equation
[OH-].[K+].[O:3]1[C:7]2=[N:8][C:9]([C:17]([O:19]CC)=[O:18])=[C:10]([C:12]([O:14]CC)=[O:13])[CH:11]=[C:6]2[CH:5]=[CH:4]1.CC(C)=O>O.C(O)C>[O:3]1[C:7]2=[N:8][C:9]([C:17]([OH:19])=[O:18])=[C:10]([C:12]([OH:14])=[O:13])[CH:11]=[C:6]2[CH:5]=[CH:4]1

Participants

6

Reactant 3

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 13849598Diethyl furo[2,3-b]pyridine-5,6-dicarboxylate

Product 1

HCID 13752512Furo[2,3-b]pyridine-5,6-dicarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Potassium hydroxide (5.60 g, 85%, 0.087 mol) in water (5 mL) is added to a stirred suspension of diethyl furo[2,3-b]pyridine-5,6-dicarboxylate (9.3 g, 0.035 mol) in absolute ethanol (100 mL). The reaction mixture is heated at 60° C. for one hour, then cooled and anhydrous acetone added. The precipitate is filtered off, dried, suspended in dry acetone and treated with hydrogen chloride to adjust to a pH of 2. Crystallization of the isolated solids from an ethyl acetate-acetone mixture affords furo[2,3-b]pyridine-5,6-dicarboxylic acid mp 189°-192° C.

Workup

  1. temperaturecooled
  2. filtrationThe precipitate is filtered off
  3. customdried
  4. additiontreated with hydrogen chloride
  5. customCrystallization of the isolated solids from an ethyl acetate-acetone mixture

Sources & evidence

ORD record
ord-90e327b44cc647d49c44b9ecf151d8db
Source dataset
uspto-grants-1990_04
Patent number
US04920226

Reaction notes

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