Water → HCID 86630356, compound

HRID 1692591Notes

Reaction equation

HRID 1692591 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][N+:18]([O-])=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.P(Cl)(Cl)([Cl:24])=O>>[CH2:1]([N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[CH:17][N:18]=[C:19]([Cl:24])[C:12]=2[O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 67280098HCID 67280098, compound

Product 1

HCID 86630356HCID 86630356, compoundYield 94%

Procedure

A solution of the compound (0.23 g) obtained in step 4 in phosphorus oxychloride (1.0 mL) was stirred at 80° C. for 30 min. The reaction mixture was poured into water, and the resultant product was extracted twice with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine, and concentrated. The residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane) to give 4-benzyl-9-chloro-3,4-dihydropyrido[4,3-f][1,4]oxazepin-5(2H)-one (0.23 g, 94%) as a colorless oil.

Workup

  1. extractionthe resultant product was extracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and brine
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (solvent gradient; 5→20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-81c9f2509f1a47d89f0d7d207c2a306f
Source dataset
uspto-grants-2012_04
Patent number
US08158617B2

Reaction notes

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