Sodium Carbonate → (3-Cyanopyridin-2-ylamino)-acetic acid ethyl ester
Reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH2:11]([O:13][C:14](=[O:17])[CH2:15][NH2:16])[CH3:12].C(=O)([O-])[O-].[Na+].[Na+].[F-].[K+]>O.CS(C)=O>[CH2:11]([O:13][C:14](=[O:17])[CH2:15][NH:16][C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1)[CH3:12]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 120 °C
Procedure
2-Chloro-3-cyanopyridine (10.0 g, 72 mmol) was dissolved into anhydrous DMSO (200 ml). Glycine ethyl ester hydrochloride (11 g, 79 mmol) and sodium carbonate (4.5 g, 42 mmol) were added and the mixture was stirred for 10 min under argon. Potassium fluoride (4.2 g, 72 mmol) was added and the mixture was heated to 120° C. for 48 h. The mixture was cooled to room temperature and added to water (400 mL). The crude product was extracted with CH2Cl2 (4×100 mL), dried over MgSO4 and concentrated to an orange solid which was purified by silica gel (CH2Cl2) to give an orange solid (7.5 g, 51%). 1H NMR (300 MHz, CDCl3) δ 8.27 (dd, J=5.0, 2.0 Hz, 1H), 7.69 (dd, J=7.6, 2.0 Hz, 1H), 6.66 (dd, J=7.6, 5.0 Hz, 1H), 5.70 (bs, 1H), 4.21-4.28 (m, 4H), 1.29 (t, J=7.2 Hz, 3H); ESI MS m/z 206 [C10H11N3O2+H]+.
Workup
- temperatureThe mixture was cooled to room temperature
- extractionThe crude product was extracted with CH2Cl2 (4×100 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated to an orange solid which
- customwas purified by silica gel (CH2Cl2)
Sources & evidence
- ORD record
- ord-ba249699dce94a308aef79611d7af016
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08450307B2
Reaction notes
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