Methylamine → HCID 19369766, compound

HRID 849219Notes

Reaction equation

HRID 849219 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:16]=3[N:15]=[C:14](Cl)[C:13]=2[CH2:12][CH2:11]1.[CH3:30][NH2:31]>O>[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][CH:18]=[C:17]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[C:16]=3[N:15]=[C:14]([NH:31][CH3:30])[C:13]=2[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 19369819HCID 19369819, compound

Product 1

HCID 19369766HCID 19369766, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

1-(2-Methyl-4-methoxyphenyl)-4-chloro-6-β,β,β-trifluoroethoxy-2,3-dihydropyrrolo[3,2-c]quinoline(600 mg, 1.42 mmol) was dissolved in aqueous solution of methylamine(40%, 5.0 ml) in the pressure tube, and the reaction mixture was refluxed at 180° C. for 15 hours. 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=1:2) to obtain 450 mg of desired compound as solid in 76% 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=1:2)

Sources & evidence

ORD record
ord-a63ea7aea34444f8ba3846b4ae80a864
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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