1-Bromo-2-Chloroethane → 1-(Quinolin-6-yl)cyclopropanecarbonitrile

HRID 1099057Notes

Reaction equation

HRID 1099057 reaction equation
[OH-].[Na+].Br[CH2:4][CH2:5]Cl.[N:7]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][C:18]#[N:19])=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3([C:18]#[N:19])[CH2:5][CH2:4]3)=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 21992552(Quinolin-6-yl)acetonitrile

Product 1

HCID 668128401-(Quinolin-6-yl)cyclopropanecarbonitrileYield 96%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

60 mL of 50% aqueous NaOH was added to a mixture of 1-bromo-2-chloroethane (22.0 mL, 0.265 mol), quinolin-6-ylacetonitrile (16.0 g, 0.0666 mol), and benzyltriethylammonium chloride (0.99 g, 0.0043 mol) at 50° C. The mixture was stirred at 50° C. for 3 h. After cooling to RT, the reaction mixture was poured into 100 ml of water, and extracted with DCM (3×100 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered through a pad of silica gel and washed with ethyl acetate in DCM (20%). The filtrate was concentrated to give the crude product 1-quinolin-6-ylcyclopropanecarbonitrile (12.4 g, 96%) which was directly used in the next step without further purification.

Workup

  1. temperatureAfter cooling to RT
  2. extractionextracted with DCM (3×100 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered through a pad of silica gel
  5. washwashed with ethyl acetate in DCM (20%)
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0a3565002521440ca8d750e627d3c973
Source dataset
uspto-grants-2012_03
Patent number
US08143251B2

Reaction notes

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