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

HRID 48209

반응식

HRID 48209 반응식
[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]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 8169835-Bromo-8-nitroisoquinolineHCID 4311764Sodium borohydride2회

생성물 1

HCID 69895026N-ethyl-5-bromo-8-nitrotetrahydroisoquinoline수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-14bfbef9101f44bfbc8c35dd9bfd29e6
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06703391B2

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