Hydrochloric Acid → 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile

HRID 2251643ノート

反応式

HRID 2251643 の反応式
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[CH2:11][CH2:10]3)=[CH:5][CH:4]=[C:3]1[C:17]#[N:18].[I-].[Sm+3].[I-].[I-].[C:23](Cl)(=[O:25])[CH3:24].Cl>C(#N)C>[C:23]([C:5]1[CH:4]=[C:3]([C:17]#[N:18])[N:2]([CH3:1])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2)(=[O:25])[CH3:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 10230237Samarium(III) iodideHCID 249870181-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile

生成物 1

HCID 249870194-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile収率 9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
120 °C

実験手順

To a stirred solution of 1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile (0.25 g, 1.0 mmol) in acetonitrile (25 mL) was added samarium iodide (0.5 g, 1.2 mmol) and acetyl chloride (1.75 mL, 24.6 mmol). The reaction mixture was heated in microwave to 120° C. for 10 minutes. The mixture was treated with a 10% aqueous HCl solution (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (30% ethyl acetate in hexane) to give 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile as a tan solid (0.025 g, 8%). MS (ESI) m/z 279; HRMS: calcd for C17H14N2O2+H+, 279.1128; found (ESI, [M+H]+), 279.1125.

後処理

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column (30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-8bf401ec560c4ccc93e2760da1f40ff4
出典データセット
uspto-grants-2008_01
特許番号
US07319152B2

反応ノート

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