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

HRID 500147

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

Conditions

Temperature: 50 °C

Procedure

60 mL of 50% aqueous sodium hydroxide was added to a mixture of 1-bromo-2-chloroethane (22.0 mL, 265 mmol), quinolin-6-ylacetonitrile (16.0 g, 66.6 mmol), and benzyltriethylammonium chloride (990 mg, 4.3 mmol) at 50° C. The reaction mixture was stirred at 50° C. for 3 h. After cooling to RT, the reaction mixture was poured into 100 mL water, and extracted with dichloromethane (3×100 mL). The combined organic extracts were dried over sodium sulfate, filtered through a pad of silica gel eluting with 20% ethyl acetate in dichloromethane. The filtrate was concentrated to give the desired product which was used in the next step without further purification. (12.4 g, 96%).

Workup

temperatureAfter cooling to RT
extractionextracted with dichloromethane (3×100 mL)
dry with materialThe combined organic extracts were dried over sodium sulfate
filtrationfiltered through a pad of silica gel eluting with 20% ethyl acetate in dichloromethane
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-ed80d26b07bf4ccabaf75272fc1f10e9
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Linked notes

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