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Sodium Iodide → 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid

HRID 506971
ノート
印刷プレビュー

反応式

HRID 506971 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[OH-].[Na+]>CC(C)=O>[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]([C:13]3[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=3[CH3:22])[C:16]([OH:18])=[O:17])[C:9]2=[O:12])=[CH:4][CH:3]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 670185873-(7-hydroxy-1-oxo-1H-isoquinolin-2-yl)-4-methylbenzoic acid

生成物 1

HCID 670185793-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid
収率 39.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3-(7-Hydroxy-1-oxoisoquinolin-2(1H)-yl)-4-methylbenzoic acid (0.47 g), 2-dimethylaminoethyl chloride hydrochloride (0.69 g), potassium carbonate (2.21 g), and sodium iodide (24 mg) were stirred in acetone (25 ml) at 60° C. for 17 hours. 2N NaOH (5 ml) was added, the reaction stirred for 20 minutes and the acetone removed by evaporation. The residue was acidified with concentrated hydrochloric acid and the solution was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK) using initially methanol and then a 99:1 mixture of methanol and aqueous ammonia solution to give 3-[7-[2-(dimethylamino)ethoxy]-1-oxoisoquinolin-2(1H)-yl]-4-methylbenzoic acid as an oil (232 mg); Mass Spectrum: M+H+ 367.

後処理

  1. customthe acetone removed by evaporation
  2. customthe solution was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  3. additiona 99:1 mixture of methanol and aqueous ammonia solution

出典と根拠

ORDレコード
ord-f3edd1e983664c16b0a39fbb47792d7a
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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