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

HRID 710306Notes

Reaction equation

HRID 710306 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-43265e7603ad43aaa088974e93f33a58
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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