Reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH:20]([CH3:22])[CH3:21])[C:7]1[C:16]([N+:17]([O-])=O)=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][N:8]=1)C.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH:20]([N:6]1[CH2:5][C:4](=[O:3])[NH:17][C:16]2[CH:15]=[C:10]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[N:8][C:7]1=2)([CH3:22])[CH3:21]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
Methyl 6-((2-ethoxy-2-oxoethyl)(isopropyl)amino)-5-nitronicotinate (2.39 g, 7.35 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (15.0 mg, 1.13 mmol), triphenyl phosphite (aprox 10 ul, 0.032 mmol), and Pt/C (240 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (110 psi) and stirred at room temperature for 16 h. The reaction was then depressurized and diluted with dichloromethane (80 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×20 mL). The filtrate was concentrated to yield the title compound (1.70 g, 93%) as a white solid. [M+H] calc'd for C12H15N3O3, 250; found, 250.
Workup
- temperaturewas then refluxed for 30 min
- filtrationThe hot solution was filtered through a pad of celite
- washwashed with hot dichloromethane (3×20 mL)
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-8a7e0a7fb65b4b06905715009d7a2392
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07928105B2
Linked notes
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