2-(2-Aminobenzoyl)benzoic acid → 5H-Dibenz(b,e)azepine-6,11-dione

HRID 1938204Notes

Reaction equation

HRID 1938204 reaction equation
[CH:1]1[CH:6]=[C:5]([C:7]([C:9]2[C:14]([NH2:15])=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[C:4]([C:16]([OH:18])=O)=[CH:3][CH:2]=1>C1(C)C(C)=CC=CC=1>[CH:10]1[C:9]2[C:7](=[O:8])[C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][C:4]=3[C:16](=[O:18])[NH:15][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 1

HCID 708472-(2-Aminobenzoyl)benzoic acid

Product 1

HCID 708365H-Dibenz(b,e)azepine-6,11-dioneYield 97.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 48.52 g (0.20 mol) of 2-aminobenzophenone-2'-carboxylic acid and 500 ml of xylene is refluxed for 67 hours, cooled to room temperature and filtered. The solid is washed with xylene to give 43.3 g (97.8%) of 5H-dibenz[b,e]azepine-6,11-dione as light tan crystals, m.p. 245°-248° C. To 4.46 g (0.020 mol) of the preceding compound in 25 ml of tetrahydrofuran is added 12 ml (0.12 mol) of a 10 molar solution of boron-dimethylsulfide in tetrahydrofuran. An additional 10 ml of tetrahydrofuran is added and the mixture is stirred overnight and then is refluxed (solids dissolve) for 4 hours. The solution is cooled and 15 ml of methanol added dropwise. The mixture is concentrated under vacuum, 50 ml of 2N sodium hydroxide is added and the mixture refluxed for 2 hours. The solid is filtered, washed with water, air dried and extracted with dichloromethane. The extract is dried (Na2SO4) and the solvent removed to give 3.25 g (83%) of crystals, m.p. 117°-122° C.

Workup

  1. temperatureis refluxed for 67 hours
  2. filtrationfiltered
  3. washThe solid is washed with xylene

Sources & evidence

ORD record
ord-2d2b9e40df91422c8db74f3a617f905e
Source dataset
uspto-grants-1997_12
Patent number
US05693635

Reaction notes

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