Dimethylamine → HCID 11371372, compound

HRID 1071842Notes

Reaction equation

HRID 1071842 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2Cl.[CH3:20][NH:21][CH3:22].O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)[CH:6]=[C:5]2[N:21]([CH3:22])[CH3:20]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 11209906HCID 11209906, compound

Product 1

HCID 11371372HCID 11371372, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

6-Bromo-4-chloro-2-(3-fluorophenyl)-quinoline (20 g, 59.4 mmoles) was placed in a 500 mL three-neck round-bottom flask equipped with magnetic stirrer, nitrogen inlet, gas outlet, condenser and heating bath and dissolved in 150 mL of N-methylpyrrolidinone. 250 mL of a 40% aq. solution of dimethylamine was added with stirring. The mixture was warmed to 60° C. for 48 hrs. At the end of this time the mixture was cooled, added to 3 L of water in a 4 L Erlenmeyer flask and the mixture stirred until solids formed. The solids were collected by vacuum filtration and dried in a vacuum oven. The product was recrystallised from ethanol in a −20° C. freezer to give 19.6 g (95%) yield of the desired product.

Workup

  1. customequipped with magnetic stirrer, nitrogen inlet, gas outlet, condenser
  2. temperatureheating bath
  3. temperatureAt the end of this time the mixture was cooled
  4. stirringthe mixture stirred until solids
  5. customformed
  6. filtrationThe solids were collected by vacuum filtration
  7. customdried in a vacuum oven
  8. customThe product was recrystallised from ethanol in a −20° C. freezer

Sources & evidence

ORD record
ord-a92bdf0d5b5e4267a9d44c3d183e091a
Source dataset
uspto-grants-2005_06
Patent number
US06906193B2

Reaction notes

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