2-Aminopyridine → 2-Chloromethyl-imidazo(1,2-A)pyridine

HRID 584377ノート

反応式

HRID 584377 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][CH2:9][C:10](=O)[CH2:11]Cl>C(#N)C>[Cl:8][CH2:9][C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:11]=1

参加物

4

反応物 2

HCID 104392-AminopyridineHCID 107931,3-Dichloroacetone

生成物 1

HCID 9576142-Chloromethyl-imidazo(1,2-A)pyridine収率 34%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2-aminopyridine (12.5 g), 1,3-dichloro-2-propanone (17.7 g) and acetonitrile (100 ml) was heated under reflux for 2 hours and concentrated. An aqueous saturated solution of sodium bicarbonate was added to the residue and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain crystals from an ethyl acetate-hexane (3:2, v/v)-eluted fraction. Recrystallization from ethyl acetate-hexane gave 2-chloromethylimidazo[1,2-a]pyridine (7.52 g, yield 34%) as pale-yellow crystals. m.p. 93-94° C.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. concentrationconcentrated
  4. additionAn aqueous saturated solution of sodium bicarbonate was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto obtain crystals from an ethyl acetate-hexane (3:2, v/v)-eluted fraction
  10. customRecrystallization from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-9e398ce4a93e48f8a40c8bd6c3131c00
出典データセット
uspto-grants-2005_08
特許番号
US06924300B2

反応ノート

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