Phenyl Salicylate → Pyrido[2,3-b][1,4]benzoxazepin-6(5H)-one

HRID 1457650Notes

Reaction equation

HRID 1457650 reaction equation
[C:1](OC1C=CC=CC=1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[NH2:17][C:18]1[C:19](Cl)=[N:20][CH:21]=[CH:22][CH:23]=1>ClC1C=CC(Cl)=CC=1Cl>[N:20]1[C:19]2[O:4][C:3]3[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=3[C:1](=[O:9])[NH:17][C:18]=2[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 8361Phenyl SalicylateHCID 805282-Chloro-3-pyridylamine

Product 1

HCID 11820483Pyrido[2,3-b][1,4]benzoxazepin-6(5H)-oneYield 28.3%

Reagents, catalysts & solvents 1

HCID 131,2,4-TrichlorobenzeneSolvent

Procedure

A mixture of 21.4 g of phenyl salicylate, 25.71 g 3-amino-2-chloropyridine and 20 ml of 1,2,4-trichlorobenzene is refluxed for 1 hour under argon and the liberated phenol and HCl simultaneously distilled (from the refluxing mixture) and collected in a solution of 1N NaOH. The hot mixture is poured into 200 ml of ethanol and the precipitated solid collected by filtration. The solid is washed with ethanol and dried Recrystallization from methanol--DMF (6:1) gives 6.0 g of product, m.p. 268°-270° C.

Workup

  1. temperatureis refluxed for 1 hour under argon
  2. distillationthe liberated phenol and HCl simultaneously distilled (from the refluxing mixture) and
  3. customcollected in a solution of 1N NaOH
  4. additionThe hot mixture is poured into 200 ml of ethanol
  5. filtrationthe precipitated solid collected by filtration
  6. washThe solid is washed with ethanol
  7. customdried
  8. customRecrystallization from methanol--DMF (6:1)

Sources & evidence

ORD record
ord-a8841a7cbaf8467f8ae548ba42fe5f28
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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