Methyl iodide → 1-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline

HRID 494171노트

반응식

HRID 494171 반응식
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][NH:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O>[CH3:14][N:11]1[C:12]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:13]=2)[CH2:8][CH2:9][CH2:10]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2525137-Nitro-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 114809551-Methyl-7-nitro-1,2,3,4-tetrahydroquinoline수율 70.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 7-nitro-1,2,3,4-tetrahydroquinoline (D1) (7.03 g, 39.4 mmol) in dimethylformamide (50 ml) was added potassium carbonate (16.3 g, 118 mmol) and iodomethane (3.7 ml, 59.1 mmol) and the reaction stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue was taken up in water (400 ml) and extracted into ether (3×200 ml). The combined ether extracts were washed with brine (100 ml), dried over MgSO4 and concentrated in vacuo to give the crude product which was purified by flash column chromatography. Elution with 20-40% EtOAc/40-60° C. petroleum ether gave the title compound as an orange solid (5.35 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 7.42 (dd, 1H), 7.33 (d, 1H), 7.01 (d, 1H), 3.31 (m, 2H), 2.96 (s, 3H), 2.80 (t, 2H), 1.99 (m, 2H).

후처리

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted into ether (3×200 ml)
  3. washThe combined ether extracts were washed with brine (100 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customto give the crude product which
  7. customwas purified by flash column chromatography
  8. washElution with 20-40% EtOAc/40-60° C. petroleum ether

출처 및 근거

ORD 기록
ord-b83137af8b8d46f9a825513ad2d1533b
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538121B2

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