Phosphorus oxychloride → HCID 23498115, compound

HRID 1837332Notes

Reaction equation

HRID 1837332 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][O:16][CH3:17])[NH:9][CH:8]=[C:7]([C:18]#[N:19])[C:6]2=O.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][C:7]=1[C:18]#[N:19]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 99705581,4-Dihydro-6-methoxy-7-(2-methoxyethoxy)-4-oxo-3-quinolinecarbonitrile

Product 1

HCID 23498115HCID 23498115, compoundYield 87.5%

Procedure

A mixture of 6-methoxy-7-(2-methoxyethoxy)-4-oxo-1,4,-dihydro-3-quinolinecarbonitrile (180 mg , 0.66 mmol) and 2.02 g of phosphorous oxychloride is heated at reflux for 40 minutes then concentrated in vacuo. The residue is added to water and the pH is adjusted to 8 by the addition of aqueous sodium bicarbonate. The solids are collected by filtration, washing with water and hexane, to provide 169 mg of 4-chloro-6-methoxy-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 178-180° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 40 minutes
  3. concentrationthen concentrated in vacuo
  4. additionThe residue is added to water
  5. additionthe pH is adjusted to 8 by the addition of aqueous sodium bicarbonate
  6. filtrationThe solids are collected by filtration
  7. washwashing with water and hexane

Sources & evidence

ORD record
ord-5992dda96d1f47ba8c9682b28f399767
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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