Dimethylamine → HCID 22643244, compound

HRID 2414765Notes

Reaction equation

HRID 2414765 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2Cl)([O-:3])=[O:2].[CH3:22][NH:23][CH3:24].O>CN1C(=O)CCC1>[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH:8]=[C:7]2[N:23]([CH3:24])[CH3:22])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 22643158HCID 22643158, compound

Product 1

HCID 22643244HCID 22643244, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

6-Nitro-4-chloro-2-(3-fluoro-phenyl)-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. The material was dissolved in 150 mL of N-methyl pyrrolidinone, stirred and 250 mL of a 40% aq. solution of dimethylamine was added. The mixture was then warmed to 60° C. for 48 hrs. At the end of this time the reaction was cooled, poured into 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 reaction 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-6cdd442b9a644d7ea210f2b7b28cfa25
Source dataset
uspto-grants-2004_11
Patent number
US06815447B2

Reaction notes

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