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Sodium Iodide → 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

HRID 506973
ノート
印刷プレビュー

反応式

HRID 506973 の反応式
[CH2:1]([NH:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][C:16]([OH:22])=[CH:17][CH:18]=3)[C:13]2=[O:23])[CH:6]=1)[CH3:2].Cl.[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH3:26][N:27]([CH3:31])[CH2:28][CH2:29][O:22][C:16]1[CH:15]=[C:14]2[C:19]([CH:20]=[CH:21][N:12]([C:7]3[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=3[CH3:11])[C:4]([NH:3][CH2:1][CH3:2])=[O:24])[C:13]2=[O:23])=[CH:18][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 11674186N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide

生成物 1

HCID 116325883-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide

試薬・触媒・溶媒 1

HCID 180
Acetone
溶媒

実験手順

N-Ethyl-3-(7-hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzamide (88 mg), 2-dimethylaminoethyl chloride hydrochloride (51 mg), potassium carbonate (0.38 g), and sodium iodide (3 mg) were stirred in acetone (4 ml) at 60° C. for 17 hours. The reaction mixture was filtered, the solids washed with acetone, and the filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with 2N NaOH solution, brine, dried (magnesium sulfate) and concentrated. Purification by column chromatography on a silica-column eluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution gave 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-N-ethyl-4-methylbenzamide as a white solid; NMR Spectrum: (DMSOd6) 1.11 (t, 3H), 2.10 (s, 3H), 2.24 (s, 6H), 2.68 (t, 2H), 3.28 (m, 2H), 4.18 (m, 2H), 6.72 (d, 1H), 7.21 (d, 1H), 7.41 (d, 1H), 7.50 (d, 1H), 7.69 (s, 1H), 7.71 (d, 1H), 7.78 (s, 1H), 7.89 (d, 1H), 8.48 (s, 1H); Mass Spectrum: M+H+ 394.

後処理

  1. filtrationThe reaction mixture was filtered
  2. washthe solids washed with acetone
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with 2N NaOH solution, brine
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated
  8. customPurification by column chromatography on a silica-column
  9. washeluting with 10% methanol/ethyl acetate+1% aqueous ammonia solution

出典と根拠

ORDレコード
ord-714e12ab53134fe0bbe96d938569dd17
出典データセット
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07786115B2

反応ノート

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