Thionyl Chloride → 7-Benzyloxy-4-chloro-6-cyanoquinoline

HRID 393672Notes

Reaction equation

HRID 393672 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:24])=O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:24])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:20]#[N:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22646645HCID 22646645, compound

Product 1

HCID 226465197-Benzyloxy-4-chloro-6-cyanoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Procedure

A mixture of 7-benzyloxy-6-cyano-1,4-dihydroquinolin-4-one (3.5 g), thionyl chloride (50 ml) and DMF (10 drops) was heated at reflux for 3 hours. The volatiles were removed by evaporation and the residue was partitioned between water and methylene chloride. A saturated solution of sodium hydrogen carbonate was added until the aqueous phase became alkaline. The aqueous phase was extracted with methylene chloride, the organic phases were combined, washed with water and dried by passing through phase separating paper. Removal of the solvent by evaporation gave a solid which was triturated with ether (50 ml) and collected by filtration. The orange solid obtained was dried in a vacuum oven to give 7-benzyloxy-4-chloro-6-cyanoquinoline (2.28 g, 36% over the last two steps).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. customThe volatiles were removed by evaporation
  4. customthe residue was partitioned between water and methylene chloride
  5. additionA saturated solution of sodium hydrogen carbonate was added until the aqueous phase
  6. extractionThe aqueous phase was extracted with methylene chloride
  7. washwashed with water
  8. customdried
  9. customseparating paper
  10. customRemoval of the solvent
  11. customby evaporation
  12. customgave a solid which
  13. customwas triturated with ether (50 ml)
  14. filtrationcollected by filtration
  15. customThe orange solid obtained
  16. customwas dried in a vacuum oven

Sources & evidence

ORD record
ord-a92b10ba39224ac5a55b11e023602f50
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

Loading…