HCID 1211386, compound → Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-one

HRID 1457653Notes

Reaction equation

HRID 1457653 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12](Cl)=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:10].C[O-].[Na+]>CN(C)C=O>[N:13]1[C:12]2[O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[NH:8][C:9](=[O:10])[C:11]=2[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 1211386HCID 1211386, compoundHCID 10942334Sodium Methoxide2×

Product 1

HCID 4296293Pyrido[2,3-b][1,5]benzoxazepin-5(6H)-oneYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 13.0 g of N-(2-hydroxyphenyl)-2-chloro-3-pyridinecarboxamide and 2.82 g of sodium methoxide in 100 ml of N,N-dimethylformamide is refluxed under argon for 3 hours. Sodium methoxide (0.50 g) is added and the mixture refluxed 2 hours and then stirred at room temperature for 2 days. The solvent is removed under high vacuum and the red-brown residue triturated with cold methanol. The mixture is filtered and the solid washed with chilled methanol to give 5.0 g of white solid, m.p. 250°-253° C.

Workup

  1. temperatureis refluxed under argon for 3 hours
  2. temperaturethe mixture refluxed 2 hours
  3. customThe solvent is removed under high vacuum
  4. customthe red-brown residue triturated with cold methanol
  5. filtrationThe mixture is filtered
  6. washthe solid washed with chilled methanol

Sources & evidence

ORD record
ord-88bd20deb2ac4a0bba13a3d5e871b963
Source dataset
uspto-grants-1998_12
Patent number
US05849735

Reaction notes

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