反応 #82704

反応方程式

2-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid

sulfuric acid

→

title compound

収率 39.6%

2-Methyl-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

収率 39.6%

溶媒

ethanol

反応条件

後処理

1. 1
   温度The mixture was heated
2. 2
   温度at reflux for 5 h, during which time all of the solid
3. 3
   その他The solvent was evaporated
4. 4
   その他the residue was partitioned between aqueous 2N sodium hydroxide and ethyl acetate
5. 5
   抽出The aqueous portion was extracted with ethyl acetate
6. 6
   洗浄The combined extracts were washed (water, brine)
7. 7
   その他dried
8. 8
   その他evaporated
9. 9
   その他to yield a residue which
10. 10
    その他was purified by chromatography
11. 11
    洗浄eluting with ethyl acetate

実験手順

2-Methyl-4-(3-nitrophenyl)-5-oxo-1,4,5,6,7,8-hexahydro-3-quinolinecarboxylic acid (4.66 g) was suspended in ethanol (200 mL) with concentrated sulfuric acid (0.5 mL). The mixture was heated at reflux for 5 h, during which time all of the solid went into solution. The solvent was evaporated, and the residue was partitioned between aqueous 2N sodium hydroxide and ethyl acetate. The aqueous portion was extracted with ethyl acetate. The combined extracts were washed (water, brine), dried, and evaporated to yield a residue which was purified by chromatography, eluting with ethyl acetate, to afford the title compound as a pale yellow solid (1.6 g); mp 183°-185° C.; MS: 284 (M); 250 MHz NMR: 1.76 (s,3, CH3), 187 (m,2, CH2), 2.16 (m,2, CH2), 2.46 (m,2, CH2), 4.58 (d,1, J=4.9, CH), 4.64 (d,1, J=4.9, CH), 7.53 (t,1, 7.6, Ar), 7.62 (d, 1, J=7.6, Ar), 7.96 (s,1, Ar), 7.98 (m,1, Ar), 8.80 (s,1, NH). Analysis for C16H16N2O3 : Calculated: C, 67.59; H, 5.67; N, 9.85; Found: C, 67,44; H, 5.75; 9.56.

出典