Methylamine → HCID 19369821, compound

HRID 849202Notes

Reaction equation

HRID 849202 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.[CH3:28][NH2:29]>>[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:29][CH3:28])[C:11]=2[CH:10]=[CH:9]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 19369813HCID 19369813, compound

Product 1

HCID 19369821HCID 19369821, compound

Conditions

Temperature
180 °C

Procedure

1-(2-methylphenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(600 mg, 1.5 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 excess 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 446 mg of desired compound as solid in 77% of yield.

Workup

  1. customAfter removing the excess 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-e4f96d3c8cde4316aa43ad3c9cfd96dd
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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