Oxalyl chloride → 2-Benzoyl-6-methylpyridine

HRID 27934

反応式

HRID 27934 の反応式
[CH3:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[CH:5]=[CH:4][CH:3]=1.[C:11](Cl)(=O)[C:12](Cl)=O.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[C:8]([C:6]1[N:7]=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=1)(=[O:10])[C:12]1[CH:11]=[CH:4][CH:3]=[CH:2][CH:1]=1

参加物

5

反応物 3

HCID 65578Oxalyl chlorideHCID 702826-Methylpyridine-2-carboxylic acidHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 126232682-Benzoyl-6-methylpyridine

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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.

後処理

  1. temperaturecooling
  2. customsolvent and excess chloride are removed
  3. concentrationConcentrate
  4. temperaturecooled to ~10°
  5. temperatureThe solution is heated to 25° for 1 hour
  6. temperatureheated
  7. temperatureto reflux for 2 hours
  8. temperaturefinally cooled
  9. additionThe mixture is poured onto ice/conc
  10. washHCl, then washed with ether
  11. additionFifty Percent (50%) sodium hydroxide is added until the precipitate
  12. dissolutionis dissolved
  13. extractionThe solution is extracted with CHCl3
  14. washwashed with water
  15. customdried

出典と根拠

ORDレコード
ord-0de59541749840e78a9cd561f168b847
出典データセット
uspto-grants-1980_09
特許番号
US04224330

関連ノート

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