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

HRID 544473ノート

反応式

HRID 544473 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]>C(COC)OC.C(O)C>[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

5

反応物 2

HCID 11715BromoacetoneHCID 7376333-Pyridinecarboxaldehyde, 2-amino-

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol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 hours at room temperature and then heated at 65° with stirring for 14 hours.The solid which separates is isolated by filtration, dissolved in 800 ml absolute ethanol and heated under a reflux for 6 hours. The ethanol solvent is removed under reduced pressure and the residue treated with 138ml 6 N hydrochloric acid in 750 ml water for 0.5 hour. 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-formyl-imidazo[1,2-a]pyridine, mp 136°-139.5° C.

後処理

  1. temperatureheated at 65°
  2. stirringwith stirring for 14 hours
  3. customThe solid which separates is isolated by filtration
  4. temperatureheated under
  5. temperaturea reflux for 6 hours
  6. customThe ethanol solvent is removed under reduced pressure
  7. additionthe residue treated with 138ml 6 N hydrochloric acid in 750 ml water for 0.5 hour
  8. washThe acidic aqueous layer is washed with ether (2×300 ml)
  9. temperaturewith cooling (78 ml) 50% sodium hydroxide and 25 g sodium bicarbonate)
  10. extractionThe aqueous layer is extracted with dichloromethane
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltration
  13. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-eb2158627065455a9db7a5f6dad4c90d
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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