Methanol → 4-Hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

HRID 127517ノート

反応式

HRID 127517 の反応式
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[S:16][CH2:17][CH:18]=[CH:19][CH2:20]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.Cl.[OH:25][NH2:26]>N1C=CC=CC=1>[OH:25][N:26]=[CH:20][CH:19]1[C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[S:16][CH2:17][CH2:18]1

参加物

5

反応物 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 544806471-Phenyl-2-(4-hydroxy-2-butenylthio)indole

生成物 1

HCID 571160384-Hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole収率 84.7%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A solution of the product of the above (2) (3.71 g) in pyridine (75 ml) is heated at 110° C. for 70 minutes. After cooling, methanol (25 ml) and hydroxyamine hydrochloride (2.2 g) are added thereto. The mixture is stirred at room temperature for 50 minutes and evaporated. The residue is acidified with ice-cooled 3 N-hydrochloric acid and extracted with chloroform. The extract is evaporated to give oily residue. The residue is chromatographed on a column of silica gel and eluted with benzene. The eluate is evaporated to give 4-hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (3.28 g). The product is dissolved into tetrahydrofuran (55 ml) and lithium aluminium hydride (1.4 g) is added thereto at room temperature. The mixture is refluxed for 1 hour. Ethyl acetate, an 10% aqueous solution of sodium hydroxide and water are successively added thereto. The precipitate is collected by filtration, washed with ethyl acetate and chloroform, and added to the filtrate. The organic layer is separated, washed with water, dried and evaporated to give the free base of the title compound as an oil.

後処理

  1. temperatureAfter cooling
  2. customevaporated
  3. temperaturecooled 3 N-hydrochloric acid
  4. extractionextracted with chloroform
  5. customThe extract is evaporated
  6. customto give oily residue
  7. customThe residue is chromatographed on a column of silica gel
  8. washeluted with benzene
  9. customThe eluate is evaporated

出典と根拠

ORDレコード
ord-62687872218d4e5e965dae8133184ae0
出典データセット
uspto-grants-1981_03
特許番号
US04256640

反応ノート

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