반응 #649604

반응 방정식

2-(2-cyano-3-methylamino-4-nitro-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester

→

2-(4-amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester

수율 107.0%

용매

EtOAc

반응 조건

후처리

1. 1
   기타The flask was purged under vacuum
2. 2
   workup.ADDITIONcharged with hydrogen gas (50 psi)
3. 3
   기타has been consumed
4. 4
   여과The reaction mixture was filtered through a pad of celite
5. 5
   세척washed with EtOAc
6. 6
   농축The resulting solution was concentrated

실험 절차

To a 500 mL Parr pressure flask was added 2-(2-cyano-3-methylamino-4-nitro-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester (7.13 g, 16.5 mmol) as a solution in EtOAc (50 mL) followed by 10% palladium on carbon (1.0 g). The flask was purged under vacuum, then charged with hydrogen gas (50 psi). The flask was agitated at room temperature for while open to the ballast (caution: potential exotherm). After 8 hours, TLC analysis indicated that all starting material has been consumed. The reaction mixture was filtered through a pad of celite and washed with EtOAc. The resulting solution was concentrated to provide 2-(4-amino-2-cyano-3-methylamino-phenyl)-2-methyl-3-oxo-butyric acid ethyl ester (5.11 g, 77%) as a gray solid, which was used without further purification. 1H NMR (400 MHz, d6-DMSO) δ 6.70 (d, J=8.2 Hz, 1H), 6.33 (d, J=8.2 Hz, 1H), 6.17 (s, 2H), 4.90 (q, J1=5.1 Hz, J2=10.6 Hz, 1H), 4.21-4.15 (m, 2H), 2.95 (d, J=5.5 Hz, 2H), 2.22 (s, 3H), 1.66 (s, 3H), 1.2 (t, J=7.0 Hz, 3H).

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