Hydrochloric Acid → 2-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

HRID 489288노트

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HRID 489288 반응식
[O:1]=[C:2]1[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4][NH:3]1.I[CH2:16][CH2:17][CH2:18][CH3:19].[H-].[Na+].Cl>CN(C=O)C>[CH2:16]([N:3]1[C:2](=[O:1])[C:11]([C:12]#[N:13])=[C:10]2[C:5]([C:6](=[O:14])[CH2:7][CH2:8][CH2:9]2)=[CH:4]1)[CH2:17][CH2:18][CH3:19]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 222665143,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile

생성물 1

HCID 222664802-Butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile수율 61%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

3,8-Dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-010) (770 mg, 4.1 mmol) was dissolved in DMF (15 mL) and to the reaction mixture was added 1-iodobutane (0.51 mL, 4.5 mmol) and sodium hydride (60% oil suspension, 180 mg, 4.5 mmol), and the reaction mixture was stirred at room temperature for 3 h. To the reaction mixture was added dilute hydrochloric acid (1 mol/L, 60 mL) and the reaction mixture was extracted with ethyl acetate (150 mL), washed with brine (50 mL), dried over anhydrous magnesium sulfate, and evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (toluene/ethyl acetate) to give 2-butyl-3,8-dioxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitrile (7-011) (610 mg, 61%) as a white crystal.

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate (150 mL)
  2. washwashed with brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1094d7d993cc4f51919f32f338a979b2
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06977266B2

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