1,3-Dimethylimidazolium Iodide → HCID 22170183, 화합물

HRID 1822763노트

반응식

HRID 1822763 반응식
[H-].[Na+].Br[C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=2)[C:7]([C:18]#[N:19])=[CH:6][N:5]=1.[CH3:20][N:21]([CH3:34])[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([CH:32]=[O:33])=[CH:24][CH:23]=1.[I-].C[N+]1C=CN(C)C=1>CN(C=O)C.C(Cl)Cl.CCOC(C)=O.O>[CH3:20][N:21]([CH3:34])[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:25]([C:32]([C:4]2[C:13]3[C:8](=[CH:9][C:10]([O:16][CH3:17])=[C:11]([O:14][CH3:15])[CH:12]=3)[C:7]([C:18]#[N:19])=[CH:6][N:5]=2)=[O:33])=[CH:24][CH:23]=1

참가 물질

9

반응물 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 6080524-Dimethylamino-1-naphthaldehydeHCID 220483501-Bromo-6,7-dimethoxyisoquinoline-4-carbonitrile

생성물 1

HCID 22170183HCID 22170183, 화합물수율 44.3%

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride (11 mg, 0.26 mmol) was added to a stirred mixture of 1-bromo-6,7-dimethoxy-isoquinoline-4-carbonitrile (see example 1) (50 mg, 0.17 mmol), 4-dimethylamino-1-naphthaldehyde (51.8 mg, 0.26 mmol), 1,3-dimethylimidazolium iodide (16 mg, 0.26 mmol) in DMF (2 mL). The reaction mixture became dark color. After 1 h, water (4 mL) was added to the above mixture, and extracted with chloroform (6 mL). The extract was washed with water (4 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford a solid. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 0–40% EtOAc in methylenechloride in 30 min) afforded 1-(4-dimethylamino-naphthalene-1-carbonyl)-6,7-dimethoxy-isoquinoline-4-carbonitrile (31 mg, 41%) as a white solid. LC-MS m/e calcd for C21H18N2O5 (MH+) 379. found 379.

후처리

  1. extractionextracted with chloroform (6 mL)
  2. washThe extract was washed with water (4 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a solid

출처 및 근거

ORD 기록
ord-fcca407dfd3841d3b02d1970cbe6cff9
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07037924B2

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