4-Methoxybenzylamine → 2-(4-Methoxy-benzyl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile

HRID 2277632ノート

反応式

HRID 2277632 の反応式
CO[C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:10]#[N:11])=[CH:6][C:5]=1[CH2:12]Br.[CH2:15]([NH2:24])[C:16]1[CH:23]=[CH:22][C:19]([O:20][CH3:21])=[CH:18][CH:17]=1>C1COCC1.CCOC(C)=O>[CH3:21][O:20][C:19]1[CH:22]=[CH:23][C:16]([CH2:15][N:24]2[CH2:12][C:5]3[C:4](=[CH:9][CH:8]=[C:7]([C:10]#[N:11])[CH:6]=3)[C:3]2=[O:14])=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 754524-MethoxybenzylamineHCID 23359115Methyl 2-(bromomethyl)-4-cyanobenzoate

生成物 1

HCID 866859482-(4-Methoxy-benzyl)-1-oxo-2,3-dihydro-1H-isoindole-5-carbonitrile

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-bromomethyl-4-cyano-benzoic acid methyl ester (18.1 g, 71.24 mmol) in THF (300 mL) was added PMBNH2 (23.4 g, 178.1 mmol) at 0° C. and the reaction mixture was stirred at room temperature for 16 hours. After vacuum filtration, the filtrate was concentrated in vacuo. The residue obtained was re-dissolved in EtOAc and washed with water and brine. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to give a crude product which was purified by column chromatography (11.69 g, 56.0%) as a solid.

後処理

  1. filtrationAfter vacuum filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue obtained
  4. washwashed with water and brine
  5. customThe organic layer was dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-cbdcaed28d3548e6b0dc1e0762227c3d
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

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