Hydrochloric Acid → 2-Methylimidazo[1,2-a]pyridine-8-carbaldehyde

HRID 544470ノート

反応式

HRID 544470 の反応式
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:11][C:12](=O)[CH3:13].Cl>C(COC)OC.C(O)C.O>[CH3:13][C:12]1[N:1]=[C:2]2[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][N:9]2[CH:11]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 11715BromoacetoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

生成物 1

HCID 139002412-Methylimidazo[1,2-a]pyridine-8-carbaldehyde

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒2 回HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A mixture of 2-aminonicotinaldehyde (92.8 g, 0.76 mol) and bromoacetone (114.5 g, 0.84 mol) in dimethoxyethane (980 ml) is stirred for 2 hr. at room temperature and then heated at 65° with stirring for 14 hr. The solid which separates is isolated by filtration, dissolved in 800 ml absolute ethanol and heated under reflux for 6 hrs. The ethanol solvent isremoved under reduced pressure and the residue treated with 138 ml 6 N hydrochloric acid in 750 ml water for 0.5 hr. The acidic aqueous layer is washed with ether (2×300 ml) and basified with cooling (78 ml 50% sodium hydroxide and 25 g sodium bicarbonate). The aqueous layer is extracted with dichloromethane. The extracts are combined and dried over anhydrous sodium sulfate. Following filtration, the solvent is removed under reduced pressure to afford 2-methyl-8-formylimidazo[1,2-a]pyridine, mp 136°-139.5° C.

後処理

  1. stirringwith stirring for 14 hr
  2. customThe solid which separates is isolated by filtration
  3. temperatureheated
  4. temperatureunder reflux for 6 hrs
  5. washThe acidic aqueous layer is washed with ether (2×300 ml)
  6. temperaturewith cooling (78 ml 50% sodium hydroxide and 25 g sodium bicarbonate)
  7. extractionThe aqueous layer is extracted with dichloromethane
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltration
  10. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-7cffbc95f15649e6b9e23676620e6eba
出典データセット
uspto-grants-1984_05
特許番号
US04450164

反応ノート

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