Ethyl Acetate → HCID 58387955, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][O:12]CC)=[N:6][C:5]=1[NH2:15].C(=O)(O)[O-].[Na+].[BH4-].[Na+].C(OCC)(=O)C>Cl.C(O)C.O1CCCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][OH:12])=[N:6][C:5]=1[NH2:15]Participants
Procedure
2-Amino-6-(2-ethoxy-vinyl)-nicotinic acid methyl ester (1.07 g, 4.81 mmol) was dissolved in 5N-hydrochloric acid (25 mL), ethanol (20 mL) and tetrahydrofuran (5 mL), and the solution was stirred for 3 hours under reflux. This reaction mixture was allowed to room temperature, and neutralized with a aqueous solution of saturated sodium bicarbonate, then, sodium borohydride (1 g, 26.5 mmol) was added to this reaction mixture, which was then stirred for 20 minutes at room temperature. Ethyl acetate was added thereto, followed by filtrating through Celite pad. This filtrate was partitioned. This organic layer was separated, the solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography, and the title compound (350 mg, 1.92 mmol, 40%) was obtained as a brown oil.
Workup
- temperatureunder reflux
- customwas allowed to room temperature
- stirringwas then stirred for 20 minutes at room temperature
- filtrationby filtrating through Celite pad
- customThis filtrate was partitioned
- customThis organic layer was separated
- customthe solvent was evaporated in vacuo
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7303963a86174f958ed1843efbb8f200
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932272B2
Reaction notes
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