Methylamine → HCID 19369846, compound

HRID 849198Notes

Reaction equation

HRID 849198 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[CH2:10][CH2:9]1.[CH3:28][NH2:29]>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:29][CH3:28])[C:11]=2[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19369789HCID 19369789, compound

Product 1

HCID 19369846HCID 19369846, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

1-(2-Methylphenyl)-4-chloro-6-β,β,β-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(392 mg, 1.0 mmol) was dissolved in aqueous solution of methylamine(40%, 5.0 ml) and the reaction mixture was refluxed at 180° C. for 15 hours in the pressure tube. The reaction mixture was dissolved in water, extracted with dichloromethane, and the organic layer was washed with water 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 column chromatography(ethyl acetate:hexane=1:1) to obtain 290 mg of desired compound as solid in 75% of yield.

Workup

  1. extractionextracted with dichloromethane
  2. washthe organic layer was washed with water for 3 times
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography(ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-cd30775ed2a643ae9c194cdf9ca6bdec
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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