Methylamine → HCID 19369768, compound

HRID 849190Notes

Reaction equation

HRID 849190 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[NH:14][CH: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[CH:11]=[CH:10]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 86755019HCID 86755019, compound

Product 1

HCID 19369768HCID 19369768, compound

Conditions

Temperature
180 °C

Procedure

1-(2-Methyl-4-fluorophenyl)-4-chloro-6-trifluoromethoxy-2,3,4,5-tetrahydropyrrolo[3,2-c]quinoline(394 mg, 1.0 mmol) was dissolved in aqueous solution of methylamine (40%, 10 ml) in the pressure tube. The reaction mixture was refluxed at 180° C. for 3 hours. After removing the reaction solvent of the above mixture, 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 301 mg of desired compound as solid in 77% of yield.

Workup

  1. customAfter removing the reaction solvent of the above mixture
  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

Sources & evidence

ORD record
ord-d226e0a32ac64adc80d8addf7a3441a1
Source dataset
uspto-grants-2000_01
Patent number
US06011044

Reaction notes

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