Phosphorus oxychloride → 4-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

HRID 1934919Notes

Reaction equation

HRID 1934919 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[C:7]([C:15]#[N:16])[C:6]2=O.P(Cl)(Cl)([Cl:20])=O>>[Cl:20][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][C:7]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 111838146,7-Dimethoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Product 1

HCID 105866764-Chloro-6,7-dimethoxy-quinoline-3-carbonitrile

Conditions

Temperature
0 °C

Procedure

A stirred mixture of 20 g of 1,4-dihydro-6,7-dimethoxy-4-oxo-3-quinolinecarbonitrile and 87 ml of phosphorous oxychloride was refluxed for 2 h, cooled, and evaporated free of volatile matter. The residue was stirred at 0° C. with dichloromethane-water as solid sodium carbonate was added until the aqueous layer was pH 8. The organic layer was separated, washed with water, dried and concentrated. Recrystallization from dichloromethane gave a solid, mp 220-223° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled
  3. customevaporated free of volatile matter
  4. additionwas added until the aqueous layer
  5. customThe organic layer was separated
  6. washwashed with water
  7. customdried
  8. concentrationconcentrated
  9. customRecrystallization from dichloromethane
  10. customgave a solid, mp 220-223° C.

Sources & evidence

ORD record
ord-b57f56aa60914595b67d02430a3fc698
Source dataset
uspto-grants-2002_05
Patent number
US06384051B1

Reaction notes

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