Pyridine → 2-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinone

HRID 2386950ノート

反応式

HRID 2386950 の反応式
O=[C:2]([CH3:13])[CH2:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O.[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C.N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:14][O:15][C:16]1[CH:22]=[CH:21][C:19]([N:20]2[C:2]([CH3:13])=[CH:3][C:4]3[C:5](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:6]2=[O:8])=[CH:18][CH:17]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 7732P-AnisidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 110739652-(2-oxopropyl)benzoic Acid

生成物 1

HCID 231511792-(4-methoxyphenyl)-3-methyl-1(2H)-isoquinolinone収率 44.4%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

2-(2-oxopropyl)benzoic acid (100 mg, 0.56 mmol), 4-methoxyaniline (76 mg, 0.56 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.84 mmol) and pyridine (0.5 mL) were dissolved in chloroform (5 mL) and stirred at room temperature overnight. Chloroform was added, the organic phase was washed by aqueous citric acid solution, sodium hydrogen carbonate aqueous solution and saturated brine in that order, and dried with anhydrous sodium sulfate. The product was purified by silica gel column chromatography (hexane/ethyl acetate=10/0-3/7) to obtain the target compound (66 mg, 44%) as a light brown solid.

後処理

  1. washthe organic phase was washed by aqueous citric acid solution, sodium hydrogen carbonate aqueous solution and saturated brine in that order
  2. dry with materialdried with anhydrous sodium sulfate
  3. customThe product was purified by silica gel column chromatography (hexane/ethyl acetate=10/0-3/7)

出典と根拠

ORDレコード
ord-a1d1328edbfd407e870bcefe12265a31
出典データセット
uspto-grants-2012_09
特許番号
US08268842B2

反応ノート

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