반응 #80761

반응 방정식

6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline

ammonium nitrate

trifluoroacetic anhydride

→

title compound

수율 106.7%

6-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline

수율 106.7%

용매

chloroform

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   기타The organic layer was separated
3. 3
   세척washed with saturated aqueous sodium bicarbonate and brine
4. 4
   건조dried over magnesium sulfate
5. 5
   농축concentrated

실험 절차

To a refluxed solution of 6-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline (40 g) and ammonium nitrate (8 g, 0.1 mol) in chloroform (100 mL) was added dropwise trifluoroacetic anhydride (56.5 mL, 0.4 mol) over 40 min. The reflux was continued for 90 min and crashed ice was added. The organic layer was separated, washed with saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and concentrated to give 46 g of the title compound (quant): 1H NMR (270 MHz, CDCl3) δ8.11 and 7.99 (d and d, 1H, J=2 Hz), 7.66 and 7.61 (d and d, 1H, J=2 Hz), 5.03~5.16 and 4.74~4.85 (m and m, 1H), 4.37~4.49 and 4.13 (m and q, 2H, J=7.2 Hz), 3.72 and 3.62 (s and s, 3H), 2.44~3.02 (m, 5H), 1.65~1.80 and 1.50~1.60 (m and m, 1H), 1.42 and 1.23 (t and t, 3H, J=7.2 and 7.2 Hz).

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