Acetic Acid → N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline

HRID 48209

反応式

HRID 48209 の反応式
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[BH4-].[Na+].[C:17](O)(=O)[CH3:18]>C1COCC1>[CH2:17]([N:6]1[CH2:5][CH2:4][CH:3]2[C:8](=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[CH:11][CH:2]2[Br:1])[CH2:7]1)[CH3:18]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 8169835-Bromo-8-nitroisoquinolineHCID 4311764Sodium borohydride2 回

生成物 1

HCID 69895026N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 5-bromo-8-nitroisoquinoline (1 g, 3.95 mmol) in 20 mL THF was cooled to 0° C. and treated sequentially with sodium borohydride (0.75 g, 19.83 mmol) followed by the slow addition of acetic acid (20 mL). The reaction mixture was allowed to warm to room temperature, and an additional 2 equiv. of sodium borohydride was added. After quenching with water and treatment with sodium hydroxide solution to make basic, the reaction mixture was extracted with ethyl acetate. The organic residue was chromatographed on silica gel (25% ethyl acetate in hexane) to give the N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline (0.8 g, 70% yield).

後処理

  1. customAfter quenching with water and treatment with sodium hydroxide solution
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. customThe organic residue was chromatographed on silica gel (25% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-14bfbef9101f44bfbc8c35dd9bfd29e6
出典データセット
uspto-grants-2004_03
特許番号
US06703391B2

関連ノート

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