Hydrochloric Acid → 2-Chloro-3,3'-bipyridine

HRID 465112

反応式

HRID 465112 の反応式
CN(C)[CH:3]=[CH:4][CH:5]=[C:6]([C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1)[C:7]#[N:8].[ClH:16].C(=O)([O-])[O-].[K+].[K+].[Si]([O-])([O-])([O-])[O-].[Mg+2].[Mg+2]>C(O)(=O)C.C(OCC)(=O)C.CCCCCC>[Cl:16][C:10]1[C:9]([C:6]2[CH:7]=[N:8][CH:3]=[CH:4][CH:5]=2)=[CH:14][CH:13]=[CH:12][N:11]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 66225Magnesium orthosilicateHCID 54400662alpha-[3-(Dimethylamino)-2-propenylidene]-3-pyridineacetonitrile

生成物 1

HCID 104200582-Chloro-3,3'-bipyridine

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
60 °C

実験手順

A 3.0 g portion of α-[3-(dimethylamino)-2-propenylidene]-3-pyridineacetonitrile was dissolved in 100 ml of glacial acetic acid. Dry hydrogen chloride gas (about 2.5 g) was introduced and the solution was heated at 60° C. for 3 hours. The reaction was cooled to 20° C. and then poured onto 200 g of ice. The solution was basified with potassium carbonate and then extracted with four 100 ml portions of methylene chloride. The organic extracts were combined, dried and the solvent removed at reduced pressure, giving an oil. This oil was dissolved in ethyl acetate:hexane (1:1) and passed through a pad of hydrous magnesium silicate. The solid obtained was recrystallized from hexane, giving 2-chloro-3,3'-bipyridine as white needles, mp 92°-93.5° C.

後処理

  1. temperatureThe reaction was cooled to 20° C.
  2. extractionextracted with four 100 ml portions of methylene chloride
  3. customdried
  4. customthe solvent removed at reduced pressure
  5. customgiving an oil
  6. customThe solid obtained
  7. customwas recrystallized from hexane

出典と根拠

ORDレコード
ord-0fcd7bd756e8416cb65495eaf1fc02fb
出典データセット
uspto-grants-1985_10
特許番号
US04550166

関連ノート

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