Reaktion #443031

Reaktionsgleichung

methyl 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoate

NaOH

→

crystals

Ausbeute 90.8%

4-[(6,11-Dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]-benzoic acid

Ausbeute 90.8%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated on a steam bath for 1 hr
2. 2
   SonstigeThe solvent is removed
3. 3
   Sonstigeto give a solid
4. 4
   ExtraktionThe solid is extracted with ether (discarded)
5. 5
   workup.DISSOLUTIONThe solid is dissolved in water
6. 6
   Sonstigeto give a solid
7. 7
   FiltrationThe solid is filtered
8. 8
   Waschenwashed with water

Vorschrift

A mixture of 0.975 g of 6,11-dihydro-5H-dibenz[b,e]azepine and 0.20 g of NaH (60% in oil) in 20 ml of tetrahydrofuran is stirred at room temperature for 0.5 hr. Then 1.1 g of mono-methyl terephthalyl chloride (prepared from mono-methyl terephthalate and thionyl chloride) is added and the mixture refluxed 18 hours. The mixture is cooled, poured into ice water and filtered. The solid is triturated with dichloromethane-hexane to give 1.0 g of crystals, m.p. 182°-185° C. The preceding compound, methyl 4-[(6,11-dihydro-5H-dibenz[b,e]azepin-5-yl)carbonyl]benzoate (2.11 g), 20 ml of 2N NaOH and 20 ml of methanol is stirred overnight and then heated on a steam bath for 1 hr. The solvent is removed to give a solid. The solid is extracted with ether (discarded). The solid is dissolved in water and the solution acidified with citric acid to give a solid. The solid is filtered and washed with water to give 1.84 g of crystals, m.p. 220°-225° C.

Quelle