HCID 19369827, compound → HCID 19369810, compound

HRID 849177Notes

Reaction equation

HRID 849177 reaction equation
[CH2:1]([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)[CH3:2]>C(CN)O>[CH2:1]([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:14][CH2:15][CH2:16][OH:22])[C:12]=2[CH2:11][CH2:10]1)[CH3:2]

Participants

3

Reactant 1

HCID 19369827HCID 19369827, compound

Product 1

HCID 19369810HCID 19369810, compoundYield 127%

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Conditions

Temperature
190 °C

Procedure

1-(2-Ethylphenyl)-4-chloro-6-trifluoromethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(801 mg, 2.0 mmol) was dissolved in ethanolamine(10 ml), and the reaction mixture was refluxed at 190° C. for 3 hours. The excess solvent was removed by distillation under reduced pressure, and the residue was diluted in dichloromethane(20 ml), then 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 530 mg of desired compound as solid in 62% of yield.

Workup

  1. customThe excess 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-35685f4b36674f128415b294966756b8
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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