Methylamine → HCID 19369776, compound

HRID 849214Notes

Reaction equation

HRID 849214 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH:11]=[CH:10]1.[CH3:29][NH2:30]>>[CH3:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[C:16]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])[C:15]=3[N:14]=[C:13]([NH:30][CH3:29])[C:12]=2[CH:11]=[CH:10]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 19369840HCID 19369840, compound

Product 1

HCID 19369776HCID 19369776, compound

Conditions

Temperature
180 °C

Procedure

1-(2-Methyl-4-fluorophenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(970 mg, 2.4 mmol) was dissolved in aqueous solution of methylamine(40%, 10 ml) in the pressure tube, and the resultant was refluxed at 180° C. for 3 hours. After removing the solvent 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 810 mg of desired compound as solid in 85% of yield.

Workup

  1. customAfter removing the solvent
  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-ba39c64eb253452eb2c84bc6b8836bae
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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