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

HRID 1595721Notes

Reaction equation

HRID 1595721 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-quinoline-3-carbonitrile 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-78890348e168495ab83f77eb5affa056
Source dataset
uspto-grants-2001_09
Patent number
US06288082B1

Reaction notes

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