Phosphorus oxychloride → 4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile

HRID 1934950Notes

Reaction equation

HRID 1934950 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10](O)=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:19][CH3:20].P(Cl)(Cl)([Cl:23])=O>>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([C:10]([Cl:23])=[C:11]([C:16]#[N:17])[CH:12]=[N:13]2)=[CH:8][C:7]=1[O:19][CH3:20]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1784867617-(3-Chloropropoxy)-4-hydroxy-6-methoxyquinoline-3-carbonitrile

Product 1

HCID 112206374-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile

Procedure

A mixture of 3.5 g (12 mmol) of 7-(3-chloro-propoxy)-4-hydroxy-6-methoxy-quinoline-3-carbonitrile and 28 ml of phosphorous oxychloride was refluxed for 1.5 hr. Excess reagent was removed at reduced pressure. The residue was mixed with ice cold dilute sodium hydroxide and ethyl acetate. The mixture was extracted with a combination of ethyl acetate and tetrahydrofuran. The combined extracts were washed with a saturated solution of sodium bicarbonate, dried over magnesium sulfate, and filter through a short column of silica gel. Solvents were removed giving 3.2 g of the title compound as a pink solid that is used with additional purification.

Workup

  1. temperaturewas refluxed for 1.5 hr
  2. customExcess reagent was removed at reduced pressure
  3. additionThe residue was mixed with ice cold dilute sodium hydroxide and ethyl acetate
  4. extractionThe mixture was extracted with a combination of ethyl acetate and tetrahydrofuran
  5. washThe combined extracts were washed with a saturated solution of sodium bicarbonate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfilter through a short column of silica gel
  8. customSolvents were removed

Sources & evidence

ORD record
ord-f222bbae05664f7daf11f1f26f490d75
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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