O-Phenylenediamine → Benzo[b][1,4]benzodiazepin-6-one

HRID 220607

Reaction equation

HRID 220607 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=O)[O:4][C:2]2=O.[C:13]1(N)[CH:18]=[CH:17][CH:16]=C[C:14]=1[NH2:19]>C(O)(=O)C.O>[CH:11]1[C:1]2[C:2](=[O:4])[N:19]=[C:14]3[CH:13]=[CH:18][CH:17]=[CH:16][C:5]3=[N:6][C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 8359Isatoic Anhydride

Product 1

HCID 19781529Benzo[b][1,4]benzodiazepin-6-oneYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of isatoic anhydride (1 mol) and 1,2 phenylenediamine (1.1 mol) in aglacial acetic acid (60%) was heated at 75° C. for 3 hrs. The resulting mixture was diluted with water and solid filtered to obtained dibenzo[b,e][1,4]-diazepine-11-one in 96% yield.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-2936c68d6a464830925ee60bd4de99dd
Source dataset
uspto-grants-2012_06
Patent number
US08202989B2

Linked notes

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