1-Chloro-2-nitrobenzene → O-(o-Aminophenoxy)benzoic acid lactam

HRID 355668Notes

Reaction equation

HRID 355668 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][CH:15]=[CH:14][C:13]=1[N+:18]([O-])=O>>[CH:8]1[C:2]2[C:1](=[O:9])[NH:18][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:4][C:3]=2[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 86750311Potassium salicylaldehyde

Product 1

HCID 72374O-(o-Aminophenoxy)benzoic acid lactam

Procedure

The starting material 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-chloronitrobenzene, followed by oxidation to the carboxylic acid, reduction of nitro, and finally ring closure, to yield the desired starting material.

Workup

  1. customto yield the

Sources & evidence

ORD record
ord-9519089090734e9f908f4bf9173e37f5
Source dataset
uspto-grants-1998_11
Patent number
US05834459

Reaction notes

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