Ammonia → HCID 22132632, compound

HRID 1857227Notes

Reaction equation

HRID 1857227 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])[N:9]=[CH:8][CH:7]=[C:6]2[CH:15]([C:18]1[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=1)C#N.N.Cl>S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[CH2:15][C:18]1[CH:19]=[CH:20][C:21]([Br:24])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 22132809HCID 22132809, compound

Product 1

HCID 22132632HCID 22132632, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

2-(6,7-Dimethoxy-4-quinolyl)-2-(4-bromophenyl)acetonitrile (850 mg) obtained in Example 161 was dissolved in 60% aqueous sulfuric acid (5 ml), and the solution was refluxed with heat for 1 hour and then poured into a container with ice and aqueous ammonia. The solution was neutralized with hydrochloric acid and extracted with methylene chloride. After drying with anhydrous sodium sulfate and removing the solvent by distillation, the resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1) to obtain 260 mg of the title compound (yield: 33%).

Workup

  1. temperaturethe solution was refluxed
  2. temperaturewith heat for 1 hour
  3. extractionextracted with methylene chloride
  4. dry with materialAfter drying with anhydrous sodium sulfate
  5. customremoving the solvent
  6. distillationby distillation
  7. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1)

Sources & evidence

ORD record
ord-e7ea01fe65834eecaac6bd2e3dbf034f
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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