HCID 19369808, compound → HCID 19369812, compound

HRID 849225Notes

Reaction equation

HRID 849225 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:14]=3[N:13]=[C:12](Cl)[C:11]=2[CH:10]=[CH:9]1>C(CN)O.O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:14]=3[N:13]=[C:12]([NH:13][CH2:14][CH2:15][OH:21])[C:11]=2[CH:10]=[CH:9]1

Participants

4

Reactant 1

HCID 19369808HCID 19369808, compound

Product 1

HCID 19369812HCID 19369812, compoundYield 171.9%

Reagents, catalysts & solvents 2

HCID 700EthanolamineSolventHCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

1-(2-Methylphenyl)-4-chloro-6-β,β,γ,γ,γ-pentafluoropropyloxypyrrolo[3,2-c]quinoline(600 mg, 1.4 mmol) was dissolved in ethanolamine(5.0 ml), then stirred at 180° C. for 15 hours in the pressure tube. The reaction mixture was dissolved in water, extracted with dichloromethane, and the organic layer was washed with water for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography(ethyl acetate:hexane=1:1) to obtain 560 mg of desired compound as solid in 89% of yield.

Workup

  1. extractionextracted with dichloromethane
  2. washthe organic layer was washed with water for 3 times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography(ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-9e3e935552a64c289a9856747d68480b
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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