Triethylamine → Ethyl 2-[(3-nitropyridin-2-YL)amino]acetate
Reaction equation
C([N:3](CC)CC)C.[N+:8]([C:11]1[CH:19]=[CH:18][C:14](C(Cl)=O)=C[CH:12]=1)([O-:10])=[O:9].[CH2:20]([O:22][C:23](=[O:33])[CH2:24][NH:25]C1C(N)=CC=CN=1)[CH3:21]>O1CCCC1.[Pd]>[CH2:20]([O:22][C:23](=[O:33])[CH2:24][NH:25][C:12]1[C:11]([N+:8]([O-:10])=[O:9])=[CH:19][CH:18]=[CH:14][N:3]=1)[CH3:21]Participants
Procedure
Under a nitrogen atmosphere, triethylamine (14.9 g, 0.148 mole) and 4-nitrobenzoyl chloride (27.5 g, 0.148 mole) in tetrahydrofuran (25 ml) were added simultaneously (dropwise) to a stirred and chilled (5°-10° C.) solution of freshly prepared N-(3-amino-2-pyridinyl)glycine ethyl ester (0.14 mole), obtained by 5% palladium on carbon hydrogenation of N-(3-nitro-2-pyridinyl) glycine ethyl ester at room temperature, in dry tetrahydrofuran (140 ml). The reaction mixture was stirred at room temperature under nitrogen overnight and the solvent was evaporated under reduced pressure. The resulting solid was triturated in water (200 ml) and saturated sodium bicarbonate solution (200 ml). The solid was filtered off, rinsed with water and dried under vacuum at 50° C. to give 50.5 g (95%) of yellow solid. A 2.0-g sample was recrystallized from isopropyl alcohol to give 1.5 g of yellow solid, mp. 151°-154° C.
Sources & evidence
- ORD record
- ord-611fa954a92346a28d127296aa78ce06
- Source dataset
- uspto-grants-1990_08
- Patent number
- US04948800
Reaction notes
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