HCID 68793755, compound → 5-Chloro-6-(quinolin-3-yloxy)pyridin-3-amine

HRID 2388040Notes

Reaction equation

HRID 2388040 reaction equation
[Cl:1][C:2]1[C:3]([O:11][C:12]2[CH:13]=[N:14][C:15]3[C:20]([CH:21]=2)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:4][CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[N:4][C:3]=1[O:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

3

Reactant 1

HCID 68793755HCID 68793755, compound

Product 1

HCID 687907985-Chloro-6-(quinolin-3-yloxy)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-Chloro-2-quinoloxy-5-nitropyridine (2.51 g, 8.34 mmol) (obtained in step iii), in ethyl acetate (50 mL) was added stannous chloride dihydrate (7.52 g, 33.36 mmol) at room temperature. Stirring was continued further for 18 hours. Removed the solvent under vacuum and chloroform (50 mL) was added. To the stirred mixture was added 1N sodium hydroxide solution until a clear solution was obtained. Separated the organic layer and extracted with chloroform. The chloroform layer was washed with brine and water successively, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, gradient 30-50% ethyl acetate in pet ether) to obtain the title compound.

Workup

  1. customRemoved the solvent under vacuum and chloroform (50 mL)
  2. additionwas added
  3. additionTo the stirred mixture was added 1N sodium hydroxide solution until a clear solution
  4. customwas obtained
  5. customSeparated the organic layer
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with brine and water successively
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under vacuum
  10. customThe crude product was purified by column chromatography (silica gel, gradient 30-50% ethyl acetate in pet ether)

Sources & evidence

ORD record
ord-150e4e26f6a44adfa08521b5b2cdd76a
Source dataset
uspto-grants-2012_09
Patent number
US08269010B2

Reaction notes

Loading…