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

HRID 1657227ノート

反応式

HRID 1657227 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-748ceb14d8c04503a89a3ff113d42045
出典データセット
uspto-grants-1993_10
特許番号
US05256782

反応ノート

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