Ethyl-[2-amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate → Ethyl-[2,3-diamino-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate
Reaktionsgleichung
[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([NH2:23])[C:14]=1[N+:24]([O-])=O)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:27])[N:5]([C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[N:16]=[C:15]([NH2:23])[C:14]=1[NH2:24])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2]Komponenten
4
Versuchsvorschrift
Crude ethyl-[2-Amino-3-nitro-6-(trifluoromethyl)-pyridin-4-yl]-benzylcarbamate (65 gm, 170 mmol) was dissolved in ethanol (1000 mL) and 10% Pd—C (6 gm) was added. Hydrogenation at 40° C. and 40 psi for 1 hour gave complete reduction of the nitro group. The catalyst was removed by filtration and the filtrate evaporated to dryness under reduced pressure to give a light brown semi-solid. Trituration with t-butyl methyl ether (150 mL) followed by filtration and washing with the same solvent (30 mL) gave the title compound (36 gm, 60% yield) as a white solid.
Aufarbeitung
- customHydrogenation at 40° C. and 40 psi for 1 hour gave complete reduction of the nitro group
- customThe catalyst was removed by filtration
- customthe filtrate evaporated to dryness under reduced pressure
- customto give a light brown semi-solid
- filtrationTrituration with t-butyl methyl ether (150 mL) followed by filtration
- washwashing with the same solvent (30 mL)
Quellen und Nachweise
- ORD-Eintrag
- ord-7ee4cef4a7bc483a943dc97f84b91d56
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07691877B2
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