HCID 19369813, compound → 220853-85-0

HRID 849203Notes

Reaction equation

HRID 849203 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:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12](Cl)[C:11]=2[CH:10]=[CH:9]1>C(CN)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:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12]([NH:13][CH2:14][CH2:15][OH:21])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 1

HCID 19369813HCID 19369813, compound

Product 1

HCID 9866521220853-85-0Yield 152.1%

Reagents, catalysts & solvents 1

HCID 700EthanolamineSolvent

Conditions

Temperature
180 °C

Procedure

1-(2-Methylphenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(391 mg, 1.0 mmol), prepared by the procedures of Step 1 and Step 2 in the Example 34, was dissolved in ethanolamine(10 ml) in the pressure tube, and the resultant was refluxed at 180° C. for 3 hours. After removing the excess ethanolamine by distillation under reduced pressure, 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 316 mg of desired compound as solid in 75% of yield.

Workup

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

Sources & evidence

ORD record
ord-87d3960b007d472a985f589cc2887cb0
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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