Triethylamine → Ethyl 2-oxo-2-(pyridin-3-ylamino)acetate
Reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.Cl[CH2:16][CH2:17][O:18][C:19](=[O:23])[C:20]([O-])=[O:21]>C(Cl)Cl>[O:21]=[C:20]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)[C:19]([O:18][CH2:17][CH3:16])=[O:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution 3-aminopyridine (3.00 g, 27.0 mmol) in methylene chloride (110 mL) at 23 ° C. was added triethylamine (7.53 mL, 54.0 mmol) and N,N-dimethylarninopyridine (330 mg, 2.70 mmol). The solution was cooled to 0° C. and chloroethyloxalate 4.42 g, 32.4 mmol) was added in a dropwise fashion. The reaction mixture was stirred at 0° C. for 2 hours and then quenched with water (30 mL) and partitioned. The organic portion was washed with 10% sodium bicarbonate solution (30 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide 4.30 g of the title compound.
Workup
- customquenched with water (30 mL)
- custompartitioned
- washThe organic portion was washed with 10% sodium bicarbonate solution (30 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-a1b7eb08f2134c03bad8806519175798
- Source dataset
- uspto-grants-2002_12
- Patent number
- US06495576B2
Reaction notes
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