Ammonia → HCID 68555276, compound

HRID 2359836Notes

Reaction equation

HRID 2359836 reaction equation
Cl[C:2]1[C:11]([C:12]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:24]>O1CCOCC1.ClCCl>[NH2:24][C:2]1[C:11]([C:12]([C:14]2[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=2[O:22][CH3:23])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 86098782HCID 86098782, compound

Product 1

HCID 68555276HCID 68555276, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

(2-Chloroquinolin-3-yl)(2,6-dimethoxyphenyl)methanone (2.0 g, 6.1 mmol) was dissolved in dioxane (15 mL), mixed with 25% aqueous ammonia solution (10 mL) and heated to 150° C. under its own pressure for 24 hours in a pressurized reactor. The reaction mixture was diluted with dichloromethane and washed several times with water. The organic phase was dried (sodium sulfate) and concentrated. The crude product was purified by chromatography (silica gel, dichloromethane, methanol). Yield: 1.15 g (3.73 mmol, 61%).

Workup

  1. washwashed several times with water
  2. dry with materialThe organic phase was dried (sodium sulfate)
  3. concentrationconcentrated
  4. customThe crude product was purified by chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record
ord-5cd720ca4e2d4fa0814a15a16cf983b7
Source dataset
uspto-grants-2014_04
Patent number
US08686002B2

Reaction notes

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