Sodium Bicarbonate → 5-Hydroxy-2-(trifluoromethyl)pyridine
Reaction equation
N[C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.N([O-])=[O:13].[Na+].C(=O)(O)[O-].[Na+]>S(=O)(=O)(O)O.O>[OH:13][C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1Participants
6
Conditions
- Temperature
- -8 °C
Procedure
3-Amino-6-trifluoromethylpyridine (9.86 g, 61 mmol) was dissolved in concentrated sulphuric acid (70 ml) and diluted with water (70 ml), then cooled to −8° C. A solution of sodium nitrite (5.18 g, 75 mmol) in water (50 ml) was slowly added, and the mixture warmed to 0° C. for 15 minutes. The solution was then poured into sulphuric acid (10 M, 250 ml) and heated to 110° C. for 1 h. After cooling, the pH was adjusted to 6 with saturated sodium bicarbonate solution, and the solution extracted with ethyl acetate (2×300 ml). The extracts were dried (MgSO4) and concentrated to give the product as a yellow solid (7.15 g, 44 mmol, 72% yield).
Workup
- temperaturethe mixture warmed to 0° C. for 15 minutes
- temperatureheated to 110° C. for 1 h
- temperatureAfter cooling
- extractionthe solution extracted with ethyl acetate (2×300 ml)
- dry with materialThe extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0e3c538aff764887bd0a5be74c4e1243
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225320B1
Reaction notes
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