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

HRID 1657227노트

반응식

HRID 1657227 반응식
[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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6212Chloroform용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-748ceb14d8c04503a89a3ff113d42045
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05256782

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