Hydrogen Peroxide → 1,2,3,4-Tetrahydro-6-iodoquinoline

HRID 710306노트

반응식

HRID 710306 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[I:11]I.OO>O>[I:11][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][CH2:4]2

참가 물질

5

반응물 3

HCID 784Hydrogen PeroxideHCID 807IodineHCID 694601,2,3,4-Tetrahydroquinoline

생성물 1

HCID 289765451,2,3,4-Tetrahydro-6-iodoquinoline수율 100.3%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a mixture of 1,2,3,4,-tetrahydroquinoline (0.34 g; 2.55 mmol) and I2 (0.32 g; 1.27 mmol) in H2O (10 ml), 30% H2O2 (0.26 ml; 2.55 mmol) was added at room temperature. The resulting mixture was vigorously stirred overnight at room temperature, and then extracted with Et2O (2×15 ml). The combined organic phase was washed with H2O, brine, dried over anhydrous MgSO4 and filtered. The filtrate was evaporated under reduced pressure and the residue was purified by FCC (SiO2; CH2Cl2), to give the title compound (0.33 g; 50%) as a creamy syrup. 1H-NMR (CDCl3) 1.84-1.92 (m, 2H); 2.69 (tr, 2H, J=6.4 Hz); 3.27 (tr, 2H, J=6.4 Hz); 3.82 (broad s, 1H); 6.22 (d, 1H, J=8.2 Hz); 7.15-7.21 (m, 2H).

후처리

  1. additionwas added at room temperature
  2. extractionextracted with Et2O (2×15 ml)
  3. washThe combined organic phase was washed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated under reduced pressure
  7. customthe residue was purified by FCC (SiO2; CH2Cl2)

출처 및 근거

ORD 기록
ord-43265e7603ad43aaa088974e93f33a58
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181182B2

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