N-Iodosuccinimide → HCID 178467033, compound
Reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1)[CH3:2].C1C(=O)N([I:18])C(=O)C1>CN(C=O)C>[CH2:1]([O:3][C:4]1[C:9]([I:18])=[CH:8][N:7]=[C:6]([OH:10])[CH:5]=1)[CH3:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of 4-ethoxypyridin-2-ol (2.5 g, 17.97 mmol) in DMF (30 mL) was added NIS (4.04 g, 17.97 mmol). The mixture was stirred at 80° C. for 16 h. The mixture was concentrated and purified by preparative HPLC (MeCN/H2O as eluants, acidic condition) to yield a yellow solid of 4-ethoxy-5-iodopyridin-2-ol (1.2 g, 4.30 mmol, 23.9% yield): 1H NMR (400 MHz, CD3OD) δ 7.70 (s, 1H), 5.92 (s, 1H), 4.15-4.10 (m, 2H), 1.48 (t, J=6.8 Hz, 3H); ES-LCMS m/z 265.8 (M+H).
Workup
- concentrationThe mixture was concentrated
- custompurified by preparative HPLC (MeCN/H2O as eluants, acidic condition)
Sources & evidence
- ORD record
- ord-e5292de4fca54c258fbd9eb4b38bee5b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382238B2
Reaction notes
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