Ethylamine hydrochloride → HCID 22386208, compound

HRID 895291Notes

Reaction equation

HRID 895291 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl[C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Cl.[CH2:18]([NH2:20])[CH3:19]>CN(C)C=O.[Cu]Br>[CH2:18]([NH:20][C:8]1[N:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])[CH3:19]

Participants

6

Reactant 3

HCID 11198Ethylamine hydrochlorideHCID 11430Potassium CarbonateHCID 762582-Chloronicotinic acid

Product 1

HCID 22386208HCID 22386208, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (9.21 g, 66.6 mmol) was added to a mixture of 2-chloronicotinic acid (5.0 g, 31.7 mol), ethylamine hydrochloride (5.18 g, 63.4 mmol) and copper (I) bromide (450 mg, 3.17 mmol) in N,N-dimethylformamide (50 ml), and the reaction heated at 100° C. for 1.5 hours, then cooled. The resulting solid was removed by filtration, and the filtrate evaporated under reduced pressure. The residual blue/green solid was triturated with acetone, and the resulting solid filtered off and dried in vacuo to afford the title compound.

Workup

  1. temperaturecooled
  2. customThe resulting solid was removed by filtration
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residual blue/green solid was triturated with acetone
  5. filtrationthe resulting solid filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-9ac6d37da21a406cafca695db99f98d1
Source dataset
uspto-grants-2005_07
Patent number
US06914160B1

Reaction notes

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