Water → HCID 13134788, compound

HRID 444330Notes

Reaction equation

HRID 444330 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18](N)=[O:19])=[CH:16][C:3]1=2.[OH-:21].[K+].O>O.C(O)C>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:19])=[O:21])=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 13134787HCID 13134787, compound

Product 1

HCID 13134788HCID 13134788, compoundYield 73.7%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To 50 mg of (5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]oxepin-8-yl)-acetamide was added 0.4 g of potassium hydroxide in 4 ml of water/ethanol (1:1), and the mixture was refluxed for 3 hours. After cooling, to this was added water, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with acetic acid and extracted with ethyl acetate. The extract was washed with water and then a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a solid, which was recrystallized from acetone to give 37 mg (yield: 72%) of (5,6-dihydro-6-oxo benzo[b]pyrido[3,2-f]oxepin-8-yl)-acetic acid as white needle crystals having a melting point of 181°-184° C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. temperatureAfter cooling
  3. washthe mixture was washed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a solid, which
  9. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-431b39908ffc4799984e9fc687c7ea80
Source dataset
uspto-grants-1981_04
Patent number
US04263437

Reaction notes

Loading…