Sodium Carbonate → HCID 19876796, compound

HRID 1886043Notes

Reaction equation

HRID 1886043 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[C:12]([NH:15][CH2:16][CH2:17][NH2:18])(=[O:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)CCO>[N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[NH:18][CH2:17][CH2:16][NH:15][C:12](=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 119282-ChloroquinolineHCID 66082N-(2-aminoethyl)acetamide

Product 1

HCID 19876796HCID 19876796, compoundYield 116.5%

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Procedure

A mixture of 2-chloroquinoline (10.00 g, 0.061 mol), N-acetylethylenediamine (6.24 g, 0.061 mol), sodium carbonate (6.48 g, 0.061 mol), and 3-methyl-1-butanol (125 mL) was heated under reflux for 3 days. The mixture was cooled, filtered, and the filtrate was concentrated to give 16.3 g (>100%) of a yellow oil. Purification by flash chromatography (eluent 5% MeOH/CHCl3 ; 10% MeOH/1% Et3N/CHCl3) gave 6.8 g (49%) of a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 days
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1b70397d624c454bba83e39458a9e1f2
Source dataset
uspto-grants-1992_09
Patent number
US05149700

Reaction notes

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