Potassium Carbonate → HCID 22646564, compound

HRID 393673Notes

Reaction equation

HRID 393673 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:22])[CH:3]=1.Cl[CH2:24][CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([NH:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 958344-(3-Chloropropyl)morpholineHCID 135673964HCID 135673964, compound

Product 1

HCID 22646564HCID 22646564, compoundYield 56.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-(4-chloro-2-fluoroanilino)-6-cyano-7-hydroxyquinoline (1 95 mg, 0.6 mmol), 4-(3-chloropropyl)morpholine (124 mg, 0.76 mol), (J. Amer. Chem. Soc. 1945, 67, 736), potassium carbonate (172 mg, 1.2 mmol) and DMF (5 ml) was heated at 100° C. for 6 hours. The mixture was cooled to ambient temperature, and was partitioned between water and methylene chloride. The organic layer was dried (MgSO4), insoluble materials were removed by filtration and silica (2 g) was added to the filtrate. The solvent was removed by evaporation and the powder obtained was purified by flash chromatography eluting with methylene chloride/methanol/ammonia (100/2/0.5 increasing to 100/20/1). Removal of the volatiles by evaporation gave an oil which was triturated with ether, collected by filtration and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-6-cyano-7-(3-morpholinopropoxy)quinoline (150 mg, 55%).

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customwas partitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried (MgSO4), insoluble materials
  4. customwere removed by filtration and silica (2 g)
  5. additionwas added to the filtrate
  6. customThe solvent was removed by evaporation
  7. customthe powder obtained
  8. customwas purified by flash chromatography
  9. washeluting with methylene chloride/methanol/ammonia (100/2/0.5 increasing to 100/20/1)
  10. customRemoval of the volatiles
  11. customby evaporation
  12. customgave an oil which
  13. customwas triturated with ether
  14. filtrationcollected by filtration
  15. customdried under vacuum

Sources & evidence

ORD record
ord-8079f430a61040488666d9079ef38b61
Source dataset
uspto-grants-2004_10
Patent number
US06809097B1

Reaction notes

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