Isatoic Anhydride → 8,9-dimethyl-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one
Reaction equation
[CH3:1][C:2]1[C:3]([NH2:10])=[C:4]([NH2:9])[CH:5]=[CH:6][C:7]=1[CH3:8].[C:11]12[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=1)NC(=O)O[C:12]2=[O:13]>C(O)(=O)C>[CH3:8][C:7]1[CH:6]=[CH:5][C:4]2[NH:9][C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=3[C:12](=[O:13])[NH:10][C:3]=2[C:2]=1[CH3:1]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
3,4-Dimethyl-1,2-phenylenediamine (0.1 mol) was dissolved in acetic acid (70%) and then isatoic anhydride (0.1 mol) was added to the solution. The resulting mixture was heated at 85° C. for 3 hrs. The mixture was poured into ice-cold water and 8,9-dimethyl-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepin-11-one was isolated (97%) by neutralization and filtration.
Workup
- additionThe mixture was poured into ice-cold water
Sources & evidence
- ORD record
- ord-ea109a5a82ea48d4ad4beb72793f8010
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08202989B2
Reaction notes
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