Chloroacetyl chloride → 2-Chloro-N-[(pyridin-2-yl)methyl]ethanimidic acid
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:15][CH2:16][C:17](Cl)=[O:18]>CC(C)=O>[Cl:15][CH2:16][C:17]([NH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 0.5 g (4.6 mmol) 2-(aminomethyl)pyridine in 10 ml acetone at 0° C. were added 1.27 g (9.2 mmol) potassium carbonate and 0.57 g (5.1 mmol) 2-chloro acetylchloride. The reaction was stirred at 0° C. until no starting material remained and then poured onto ice water. The mixture was extracted twice with ethyl acetate. The combined organic layers were washed with aqueous NaHCO3 (sat.) and brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used directly for the next step. MS(ISP): 185.21 ([MH]+.
Workup
- additionpoured onto ice water
- extractionThe mixture was extracted twice with ethyl acetate
- washThe combined organic layers were washed with aqueous NaHCO3 (sat.) and brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-62f6afb793ad4b1d9298364b1f73f3fc
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524823B2
Reaction notes
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