2,5-Dichloronitrobenzene → 2-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-one
Reaction equation
[CH:1](=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[K].Cl[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[N+:19]([O-])=O>>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]2[O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:9])[NH:19][C:13]=2[CH:14]=1Participants
3
Procedure
The starting material 8-chloro-10,11-dihydro-dibenz[b,f][1,4]oxazepin-11-one was prepared according to the procedures reported in Coyne et al (J. Med. Chem., 1967, 10:541). Briefly, this entailed coupling potassium salicylaldehyde with 2,5-dichloronitrobenzene, followed by oxidation to carboxylic acid, reduction of nitro, and finally ring closure, to yield the desired 8-chloro starting material.
Sources & evidence
- ORD record
- ord-e19f0043f5184b1b8ea158f02f942967
- Source dataset
- uspto-grants-1997_02