6-Hydroxyquinoline → HCID 47453787, compound

HRID 2264605Notes

Reaction equation

HRID 2264605 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[CH:5]2.[NH2:12][C:13]1[N:18]=[C:17](Cl)[CH:16]=[C:15]([Cl:20])[N:14]=1.[OH-].[Na+]>O.CC(C)=O>[Cl:20][C:15]1[CH:16]=[C:17]([O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[CH:5]3)[N:18]=[C:13]([NH2:12])[N:14]=1

Participants

5

Reactant 3

HCID 113746-HydroxyquinolineHCID 14798Sodium HydroxideHCID 655222-Amino-4,6-dichloropyrimidine

Product 1

HCID 47453787HCID 47453787, compound

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a mixture containing 7.25 g (0.05 mol) 6-hydroxy-quinoline, 8.25 g (0.05 mol) 2-amino-4,6-dichloropyrimidine in 300 mL of water/acetone 1:1 are added 2.0 g (0.05 mol) sodium hydroxide. On heating a clear solution is first obtained from which a thick precipitate separates. Stirring under reflux is continued for a total of 6 h. The mixture is cooled, filtered and the solid washed with acetone/water 1.1 and dried. The title compound is obtained as a solid: map. 248-250° C.; MS: [M+1]+=273; HPLC: CtRet=1.30; TLC (dichloromethane/methanol 95:5): Rf=0.46.

Workup

  1. temperatureOn heating a clear solution
  2. customis first obtained from which a thick precipitate separates
  3. temperatureunder reflux
  4. customis continued for a total of 6 h
  5. temperatureThe mixture is cooled
  6. filtrationfiltered
  7. washthe solid washed with acetone/water 1.1
  8. customdried

Sources & evidence

ORD record
ord-ab92d23a13344278bed362708f006b64
Source dataset
uspto-grants-2010_12
Patent number
US07855215B2

Reaction notes

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