7-Nitrooxindole → 7-Aminoindolin-2-one

HRID 1844103노트

반응식

HRID 1844103 반응식
[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

참가 물질

5

반응물 2

HCID 64248387-NitrooxindoleHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 64233127-Aminoindolin-2-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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]−.

후처리

  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

출처 및 근거

ORD 기록
ord-e8b9700d77af4eed8d017d91d79917ea
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946282B2

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