Sodium Dithionite → Ethyl 2-amino-2-cyanoacetate
Reaction equation
O[N:2]=[C:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O.C(=O)(O)[O-].[Na+]>[NH2:2][CH:3]([C:9]#[N:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
To a stirred solution of the ethyl (hydroxyimino)cyanoacetate (10 g, 70.4 mmol) in water and sodium bicarbonate saturated solution (80 mL) was added sodium dithionite (34.3 g, 197 mmol). The reaction was heated up to 35° C. for 3 h. The solution was then saturated with sodium chloride and extracted with ethyl acetate (3×200 mL). The combined organic phases were dried over sodium sulfate and concentrated, giving an oil of ethyl 2-amino-2-cyanoacetate (1.6 g). 1H NMR (400 MHz, CDCl3) δ 4.42 (s, 1H), 4.32 (q, 2H), 1.33 (t, 3H).
Workup
- extractionsaturated with sodium chloride and extracted with ethyl acetate (3×200 mL)
- dry with materialThe combined organic phases were dried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e55148636f8c449dabe504045adb8e6c
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829572B2
Reaction notes
Loading…