Methylamine → HCID 19369794, compound

HRID 849187Notes

Reaction equation

HRID 849187 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][C:23]([F:26])([F:25])[F:24])[C:15]=3[N:14]=[C:13](Cl)[C:12]=2[CH2:11][CH2:10]1.[CH3:28][NH2:29]>>[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][C:23]([F:26])([F:25])[F:24])[C:15]=3[N:14]=[C:13]([NH:29][CH3:28])[C:12]=2[CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 19369839HCID 19369839, compound

Product 1

HCID 19369794HCID 19369794, compound

Conditions

Temperature
190 °C

Procedure

1-(2-Methyl-4-fluorophenyl)-4-chloro-6-trifluoromethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(500 mg, 1.3 mmol) was dissolved in aqueous solution of methylamine(40%, 10 ml) in the pressure tube, and the reaction mixture was refluxed at 190° C. for 3 hours. The 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 with ethyl acetate as eluent to obtain 380 mg of desired compound as solid in 72% 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 with ethyl acetate as eluent

Sources & evidence

ORD record
ord-c8f67869527248fbaf0b0fa2ca9184e8
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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