Dimethyl Sulfoxide → 5-(4-Carboxyphenyl)-2-hydroxypyridine
Reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CS(C)=O.Cl.[NH+]1C=CC=CC=1>O>[O:2]=[C:3]1[NH:8][CH:7]=[C:6]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH:5]=[CH:4]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
4-(6-Methoxypyridin-3-yl)benzoic acid (3.34 g, 14.6 mmol), dimethylsulfoxide (6 mL), and pyridinium hydrochloride (8.43 g, 72.9 mmol) were heated together, with stirring, at 160° C. for 15 minutes. The reaction mixture was cooled to ˜90° C., and water added slowly (100 mL). The solution/suspension was cooled to 0° C., the precipitate filtered off and washed with water. The wet product was dried by azeotroping off the residual water with methanol to give the product as a white solid (2.38 g, 11.1 mmol). 1H NMR (DMSO) δ 7.93 (d, 2H), 7.91-7.78 (m, 2H), 7.68 (d, 2H), 6.43 (d, 1H). ESI MS (M+1)+: 216.
Workup
- temperatureThe reaction mixture was cooled to ˜90° C.
- temperatureThe solution/suspension was cooled to 0° C.
- filtrationthe precipitate filtered off
- washwashed with water
- customThe wet product was dried
- customby azeotroping off the residual water with methanol
Sources & evidence
- ORD record
- ord-15b4868b0e1248729b8b4713d8bf0337
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947684B2
Reaction notes
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