Methanol → 5H-Dibenz(b,e)azepine-2-acetic acid, 6,11-dihydro-11-oxo-

HRID 904204Notes

Reaction equation

HRID 904204 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([O:20]CC)=[O:19])=[CH:16][C:3]1=2.CO>O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:20])=[O:19])=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 887MethanolHCID 23333604HCID 23333604, compound

Product 1

HCID 30524835H-Dibenz(b,e)azepine-2-acetic acid, 6,11-dihydro-11-oxo-Yield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of ethyl 5,6-dihydro-11-oxodibenz[b,e]azepine-2-acetate (0.333 g), methanol (20 ml) sodium hydroxide (1 g) and water (20 ml) was heated under refluxing for 3 hours. After removal of the solvent by distillation, water was added to the mixture, and then, 5% sulfuric acid was added. The precipitated crystals were collected by filtration, washed in water, and dried to obtain 5,6-dihydro-11-oxodibenz[b,e]azepine-2-acetic acid (0.206 g). m.p.: 135°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureunder refluxing for 3 hours
  3. customAfter removal of the solvent
  4. distillationby distillation, water
  5. additionwas added to the mixture
  6. addition5% sulfuric acid was added
  7. filtrationThe precipitated crystals were collected by filtration
  8. washwashed in water
  9. customdried

Sources & evidence

ORD record
ord-4aff23e8767544cea9c782b2089eaaca
Source dataset
uspto-grants-1980_10
Patent number
US04230703

Reaction notes

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