7-Nitrooxindole → 7-Aminoindolin-2-one

HRID 1844103ノート

反応式

HRID 1844103 の反応式
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10](=[O:13])[CH2:9]2

参加物

5

反応物 2

HCID 64248387-NitrooxindoleHCID 178418361HCID 178418361、化合物

生成物 1

HCID 64233127-Aminoindolin-2-one

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

To a solution of 7-nitroindoline-2-one in methanol (1.0 gm/60 mL), added Pd/C (300 mg, 30 wt %). H2 gas maintained with pressure using hydrogen gas balloon, solution stirred for 4 hours at RT. The catalyst was removed by filtration over celite. The filtrate was concentrated in vacuo to give crude product, which was washed with diethyl ether to afford compound 7-aminoindolin-2-one; YD: 76.77%; mp: 248-251° C.; Rf: 0.6 (CHCl3:MeOH: 9.0:1.0). 1H NMR (DMSO-d6) 200 MHz, δ: 3.382 (s, 2H), 4.794 (s, 2H), 6.453-6.498 (m, 2H), 6.673 (t, J=8.0 Hz, 1H), 9.906 (s, 1H). MS (ESI): m/z 146.8 [M−H]−.

後処理

  1. temperatureH2 gas maintained with pressure
  2. customThe catalyst was removed by filtration over celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give crude product, which
  5. washwas washed with diethyl ether

出典と根拠

ORDレコード
ord-e8b9700d77af4eed8d017d91d79917ea
出典データセット
uspto-grants-2015_02
特許番号
US08946282B2

反応ノート

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