Potassium Hydroxide → 3h-Furo[2,3-f]benzoxazole-2-one-6-carboxylic acid

HRID 900783Notes

Reaction equation

HRID 900783 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]3[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[O:10][C:8]3=[CH:9][C:4]=2[NH:3][C:2]1=[O:18].[OH-].[K+]>C(O)C>[O:1]1[C:5]2[CH:6]=[C:7]3[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[O:10][C:8]3=[CH:9][C:4]=2[NH:3][C:2]1=[O:18]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22350166Ethyl 3h-furo[2,3-f]benzoxazole-2-one-6-carboxylate

Product 1

HCID 223501933h-Furo[2,3-f]benzoxazole-2-one-6-carboxylic acidYield 95.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 1.0 g (4 mmol) of ethyl 3H-furo[2,3-f]benzoxazole-2-one-6-carboxylate, 100 ml of ethanol and 0.5 g of potassium hydroxide is refluxed for 1 h. The mixture is concentrated, the residue is dissolved in water and acidified with 20% aqueous sulfuric acid solution. The precipitated crystals are filtered off and washed with water to yield 0.84 g (95%) of the title compound. Mp.: 190-192° C. (water).

Workup

  1. temperatureis refluxed for 1 h
  2. concentrationThe mixture is concentrated
  3. dissolutionthe residue is dissolved in water
  4. filtrationThe precipitated crystals are filtered off
  5. washwashed with water

Sources & evidence

ORD record
ord-337a262bfcb74b01ba27c6c8221e1566
Source dataset
uspto-grants-2008_04
Patent number
US07361670B2

Reaction notes

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