Ethylene Glycol → 1-(6-Chloropyridin-3-yl)cyclopropane-1-carboxylic acid
Reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5](CC#N)=[CH:4][CH:3]=1.Br[CH2:12][CH2:13]Cl.[OH-:15].[Na+].[CH2:17]([OH:20])[CH2:18]O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:18]2([C:17]([OH:20])=[O:15])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a stirred mixture of (6-chloropyridin-3-yl)acetonitrile (2.00 g, 0.0131 mol), benzyltriethylammonium chloride (0.2 g, 0.0008 mol), and 1-bromo-2-chloroethane (3.26 mL, 0.0393 mol), was added sodium hydroxide aqueous solution (50%, 3 mL, 0.08 mol) drop-wise at 50° C. The mixture was stirred at 50° C. for 5 h. 1,2-ethanediol (4 mL) was added to the above mixture and stirred at 100° C. overnight. The aqueous layer was acidified to pH ˜1, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried with sodium sulfate, filtered, and concentrated to afford the desired compound (2.2 g, 85%). Analytical LCMS: (M+H)+=198.0.
Workup
- stirringstirred at 100° C. overnight
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water and brine
- dry with materialdried with sodium sulfate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f7823ac989934a1582d937efc57ddc50
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683060B2
Reaction notes
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