Ammonia → HCID 68554149, compound

HRID 2359842Notes

Reaction equation

HRID 2359842 reaction equation
Cl[C:2]1[C:11]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH3:23])[CH:8]=2)[N:3]=1.[NH3:24]>O1CCOCC1.CO>[NH2:24][C:2]1[C:11]([C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH3:21])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:22][CH3:23])[CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86098787HCID 86098787, compound

Product 1

HCID 68554149HCID 68554149, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(2-Chloro-6-methoxyquinolin-3-yl)(2-methoxyphenyl)methanone (3.4 g, 10.4 mmol) was dissolved in dioxane (25 mL), mixed with 25% aqueous ammonia solution (15 mL) and heated for 30 hours to 150° C. under intrinsic pressure in the pressurized reactor. After cooling, the reaction mixture was diluted with methanol, prepurified with activated carbon and concentrated after filtration. The crude product was dissolved in dichloromethane and washed with water. The dichloromethane solution was dried (sodium sulfate) and concentrated. The crude product was purified chromatographically (silica gel, dichloromethane, 0-2% methanol). Yield: 1.4 g (4.5 mmol, 44%).

Workup

  1. temperatureheated for 30 hours to 150° C. under intrinsic pressure in the pressurized reactor
  2. temperatureAfter cooling
  3. concentrationconcentrated
  4. filtrationafter filtration
  5. dissolutionThe crude product was dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialThe dichloromethane solution was dried (sodium sulfate)
  8. concentrationconcentrated
  9. customThe crude product was purified chromatographically (silica gel, dichloromethane, 0-2% methanol)

Sources & evidence

ORD record
ord-60388bef9068407fb5619916f8fdd840
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

Loading…