HCID 19369811, compound → HCID 19369805, compound

HRID 849181Notes

Reaction equation

HRID 849181 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:26])([F:25])[F:24])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH2:11][CH2:10]1>C(CN)O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][C:23]([F:26])([F:25])[F:24])[C:15]=3[N:14]=[C:13]([NH:9][CH2:4][CH2:3][OH:2])[C:12]=2[CH2:11][CH2:10]1

Participants

3

Reactant 1

HCID 19369811HCID 19369811, compound

Product 1

HCID 19369805HCID 19369805, compoundYield 165.3%

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Conditions

Temperature
190 °C

Procedure

1-(2-methoxyphenyl)-4-chloro-6-trifluoromethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(600 mg, 1.5 mmol) was dissolved in ethanolamine(6 ml) in the pressure tube, then refluxed at 190° C. for 3 hours. The solvent was removed by distillation under reduced pressure, then the residue was diluted in dichloromethane(20 ml), and washed with water (15 ml) 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 chromatography to obtain 520 mg of desired compound as solid in 83% of yield.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionthe residue was diluted in dichloromethane(20 ml)
  3. washwashed with water (15 ml) for 3 times
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4dca2fcaa3ea494db172dd8a318d1bb4
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

Loading…