Hydrochloric Acid → 5-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine

HRID 1885202ノート

反応式

HRID 1885202 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]2[S:17][C:18]([CH2:20][CH3:21])=[CH:19][C:9]=12.Cl.O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(Cl)(Cl)Cl.O.O1CCOCC1>[NH2:14][C:13]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:9]2[CH:19]=[C:18]([CH2:20][CH3:21])[S:17][C:10]2=[N:11][CH:12]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 197871684-(2-Chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine

生成物 1

HCID 197871805-Amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine収率 85.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a mixture of 4-(2-chlorophenyl)-2-ethyl-5-nitrothieno[2,3-b]pyridine (4.0 g), dioxane (25 ml) and conc. hydrochloric acid (12.5 ml) was added tin(II) chloride dihydrate (8.5 g). After stirring at room temperature for one hour, water was added to the mixture, which was made strong alkaline with 6N NaOH and then extraced with chloroform. The extract was washed with water and dried over MgSO4 and the solvent was distilled off. The residue was chromatographed on a silica gel column and eluted with hexane-ethyl acetate (4 : 1). The solvent was distilled off and to the residue was added hexane to obtain 5-amino-4-(2-chlorophenyl)-2-ethylthieno[2,3-b]pyridine (3.1 g, 85.6%) as crystals. The crystals were recrystallized from isopropyl ether to obtain colorless prisms, mp: 87°-88° C.

後処理

  1. washThe extract was washed with water
  2. dry with materialdried over MgSO4
  3. distillationthe solvent was distilled off
  4. customThe residue was chromatographed on a silica gel column
  5. washeluted with hexane-ethyl acetate (4 : 1)
  6. distillationThe solvent was distilled off and to the residue
  7. additionwas added hexane

出典と根拠

ORDレコード
ord-dc1486e684ed400faeba6e69bfd3aee3
出典データセット
uspto-grants-1992_09
特許番号
US05143919

反応ノート

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