1-Methyl-4-phenyl-3-hydroxypyridinium Iodide → 1-Methyl-4-phenyl-3-hydroxypyridine
Reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([OH:15])[CH:4]=1>CO>[CH3:2][N:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([OH:15])[CH2:4]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A mixture of 2 (4.03 g, 12.9 mmol) and IRA-OH (400) resin (20 mL) in MeOH was stirred at 25° C. for 1 h then the basic resin was filtered off and washed several time with MeOH. The resulting clear solution was concentrated under reduced pressure to afford the compound 3 (2.21 g, 92%) as a pale yellow solid used in the next step without further purification: mp 154-157° C.; 1H NMR (DMSO-d6) δ3.97 (s, 3H), 7.3-7.52 (m, 5H), 7.38 (d, 1H, J=7.5 Hz), 8.04 (d, 1H, J=8.1 Hz), 8.053 (s, 1H).
Workup
- filtrationthe basic resin was filtered off
- washwashed several time with MeOH
- concentrationThe resulting clear solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-4b1422d08c34428d9993e4c50e2c3d89
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350758B1
Reaction notes
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