Ethylene Glycol → HCID 66662416, compound

HRID 557869Notes

Reaction equation

HRID 557869 reaction equation
[OH-:1].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](CC#N)=[CH:5][CH:4]=1.Br[CH2:17][CH2:18]Cl.[CH2:20]([OH:23])[CH2:21]O>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([C:21]2([C:20]([OH:23])=[O:1])[CH2:18][CH2:17]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 2573874-Quinolineacetonitrile

Product 1

HCID 66662416HCID 66662416, compound

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of NaOH in water (2 ml, 50%) was added to a mixture of quinolin-4-ylacetonitrile (0.5 g, 0.002 mol), 1-bromo-2-chloro-ethane (1.0 mL, 0.012 mol), and benzyltriethylammonium chloride (0.1 g, 0.0004 mol) at 50° C. After the mixture was stirred at 50° C. for 3 hours, 1,2-ethanediol (5 mL, 0.09 mol) was added. Then the reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and washed with ether (3×). The aqueous layer was acidified (pH=2), and then extracted with ethyl acetate (3×). The combined organic layer was dried over MgSO4, filtered, and concentrated to afford the desired product. LC/MS: 214.1 (M+H+).

Workup

  1. stirringThen the reaction mixture was stirred at 100° C. overnight
  2. temperatureThe reaction mixture was cooled to room temperature
  3. washwashed with ether (3×)
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b1029d289af944c9a7409c2dd6a8e34a
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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