Реакция #56212

Уравнение реакции

AlCl3

6 -methyl-2-pyridylcarboxylic acid

oxalyl chloride

→

6-benzoyl-2-methylpyridine

Растворители

benzene

Условия реакции

Обработка

1. 1
   Температураcooling
2. 2
   Другоеsolvent and excess chloride are removed
3. 3
   КонцентрированиеConcentrate
4. 4
   Температураcooled to ~10°
5. 5
   ТемператураThe solution is heated to 25° for 1 hour
6. 6
   Температураheated
7. 7
   Температураto reflux for 2 hours
8. 8
   Температураfinally cooled
9. 9
   workup.ADDITIONThe mixture is poured onto ice/conc
10. 10
    ПромывкаHCl, then washed with ether
11. 11
    workup.ADDITIONFifty Percent (50%) sodium hydroxide is added until the precipitate
12. 12
    workup.DISSOLUTIONis dissolved
13. 13
    ЭкстракцияThe solution is extracted with CHCl3
14. 14
    Промывкаwashed with water
15. 15
    Другоеdried

Методика

To 15 g of 6 -methyl-2-pyridylcarboxylic acid (122 mmol) in 200 ml benzene is added dropwise 19.1 g (150 mmol) oxalyl chloride (dissolved in 30 ml benzene) with ice bath cooling. After 1 hr, solvent and excess chloride are removed. Concentrate is taken up in 100 ml benzene, cooled to ~10° & 175 mmol AlCl3 added. The solution is heated to 25° for 1 hour, then heated to reflux for 2 hours, and finally cooled and stirred overnight. The mixture is poured onto ice/conc. HCl, then washed with ether. Fifty Percent (50%) sodium hydroxide is added until the precipitate is dissolved. The solution is extracted with CHCl3, washed with water, dried and stripped, leaving 6-benzoyl-2-methylpyridine.

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