1,3-Dimethylimidazolium Iodide → HCID 22170183、化合物

HRID 1822763ノート

反応式

HRID 1822763 の反応式
[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

参加物

9

反応物 4

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

生成物 1

HCID 22170183HCID 22170183、化合物収率 44.3%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fcca407dfd3841d3b02d1970cbe6cff9
出典データセット
uspto-grants-2006_05
特許番号
US07037924B2

反応ノート

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