6-iodo-1,2,3,4-tetrahydroquinoline synthesis
- Product Name:6-iodo-1,2,3,4-tetrahydroquinoline
- CAS Number:193354-16-4
- Molecular formula:C9H10IN
- Molecular Weight:259.09
635-46-1
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Yield:193354-16-4 50%
Reaction Conditions:
with dihydrogen peroxide;iodine in water at 20;
Steps:
9.A
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 x 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; CH2CI2), to give the title compound (0.33 g; 50%) as a creamy syrup. 1 H-NMR (CDCI3) 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, 1 H); 6.22 (d, 1 H, J = 8.2 Hz); 7.15 - 7.21 (m, 2H).
References:
WO2010/42998,2010,A1 Location in patent:Page/Page column 56
13327-31-6
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