Trifluoroacetic anhydride → 6-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline

HRID 52483

반응식

HRID 52483 반응식
[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])[CH:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:6][CH2:5]2.[N+:24]([O-])([O-:26])=[O:25].[NH4+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH2:3][CH:4]2[C:9](=[C:10]([N+:24]([O-:26])=[O:25])[CH:11]=1)[N:8]([C:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:13])[CH:7]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:6][CH2:5]2

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 22985Ammonium nitrateHCID 676514876-bromo-2-methoxycarbonylmethyl-N-ethoxalyltetrahydroquinoline

생성물 1

HCID 676513916-Bromo-2-methoxycarbonylmethyl-8-nitro-N-ethoxalyltetrahydroquinoline수율 106.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

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).

후처리

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with saturated aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-880ae8be6c3c480a916014a0acbec60d
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616586

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