3-Hydroxy-5,6-dimethylpyridine synthesis
- Product Name:3-Hydroxy-5,6-dimethylpyridine
- CAS Number:61893-00-3
- Molecular formula:C7H9NO
- Molecular Weight:123.15
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Yield:61893-00-3 3.5 g (86%)
Reaction Conditions:
with sodium chloride;sodium nitrite in aq. sulfuric acid;water;
Steps:
23.E Step E
Step E : Preparation of 5,6-Dimethyl-3-hydroxypyridine To a cold (0°C) solution of 3-amino-5,6-dimethylpyridine (4 g, 32.8 mmol) in 5% aq. sulfuric acid (100 mL), a solution of sodium nitrite (2.5 g, 36 mmol) in water (20 mL) was added dropwise. The resultant solution was stirred at 0°C for 30 min, transferred into an addition funnel maintained at 0°C with external cooling, and added dropwise into boiling 5% aq. sulfuric acid (70 mL) over a period of 30 min. The resultant solution was refluxed for additional 15 min, cooled to 0°C, neutralized with 40% aq. sodium hydroxide, saturated with addition of solid sodium chloride, and the product extracted into methylene chloride. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield 3.5 g (86%) of crude 3-hydroxy-5,6-dimethylpyridine.
References:
EP481802,1992,A1
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