Methyl 2-(4-cyano-2-nitrophenyl)acetate → 2-Oxindole-6-carbonitrile

HRID 552825

反応式

HRID 552825 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](OC)=[O:11])=[C:5]([N+:14]([O-])=O)[CH:4]=1)#[N:2]>CC(O)=O.[Fe]>[O:11]=[C:10]1[CH2:9][C:6]2[C:5](=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[NH:14]1

参加物

4

反応物 1

HCID 23076960Methyl 2-(4-cyano-2-nitrophenyl)acetate

生成物 1

HCID 27733482-Oxindole-6-carbonitrile収率 56.6%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

Methyl (4-cyano-2-nitrophenyl)acetate (128 mg) was dissolved in AcOH (3.0 ml), followed by addition of iron powders (129 mg), and the reaction solution was stirred in an oil bath at 100° C. for 1.5 hours. It was concentrated to remove AcOH, followed by addition of EtOAc. The brown solid was separated by filtration, and the organic layer was washed with a 1M HCl solution and saturated brine, dried over anhydrous MgSO4, and concentrated. The residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5) to obtain to obtain 2-oxoindoline-6-carbonitrile (52.0 mg) as a pale yellow solid.

後処理

  1. concentrationIt was concentrated
  2. customto remove AcOH
  3. additionfollowed by addition of EtOAc
  4. customThe brown solid was separated by filtration
  5. washthe organic layer was washed with a 1M HCl solution and saturated brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=99:1 to 95:5)
  9. customto obtain

出典と根拠

ORDレコード
ord-541b4f61fcf84ca78a21f45b4ff0231a
出典データセット
uspto-grants-2011_05
特許番号
US07951825B2

関連ノート

読み込み中…