Phosphorus oxychloride → HCID 21956453, compound

HRID 2213833Notes

Reaction equation

HRID 2213833 reaction equation
[CH3:1][O:2][C:3]1[C:19]([O:20][CH3:21])=[CH:18][C:6]2=[N:7][C:8]3[NH:9][CH:10]=[C:11]([C:16]#[N:17])[C:12](=O)[C:13]=3[CH:14]=[C:5]2[CH:4]=1.P(Cl)(Cl)([Cl:24])=O>CCCCCC>[Cl:24][C:12]1[C:13]2[CH:14]=[C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:19]([O:20][CH3:21])=[CH:18][C:6]3=[N:7][C:8]=2[N:9]=[CH:10][C:11]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 21956403HCID 21956403, compound

Product 1

HCID 21956453HCID 21956453, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 7,8-dimethoxy-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carbonitrile (500 mg, 1.78 mmol) and 5 mL of phosphorous oxychloride is heated at reflux for one hour then cooled to room temperature. Hexane (20 mL) is added and the resultant solids are collected by filtration washing with hexane, water, methanol and ethyl acetate to provide 258 mg (49%) of 4-chloro-7,8-dimethoxybenzo[b][1,8]naphthyridine-3-carbonitrile as a brown solid, mp>300° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for one hour
  3. filtrationthe resultant solids are collected by filtration
  4. washwashing with hexane, water, methanol and ethyl acetate

Sources & evidence

ORD record
ord-19b7c53b650e4ad29e6c920e1fb88afb
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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