5-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione → 5-(4-Aminophenoxy)isoindoline-1,3-dione

HRID 491066노트

반응식

HRID 491066 반응식
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1)([O-])=O>CC(O)=O.O.[Fe]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([O:8][C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[C:14](=[O:18])[NH:13][C:12]3=[O:19])=[CH:6][CH:5]=1

참가 물질

5

반응물 1

HCID 8675015-(4-Nitrophenoxy)-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 8826275-(4-Aminophenoxy)isoindoline-1,3-dione수율 75%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 962Water용매2회

실험 절차

A solution of 5-(4-nitrophenoxy)isoindoline-1,3-dione (0.6 g, 2.11 mmol) in conc. AcOH (12 mL) and water (0.1 mL) was stirred under stream of argon while iron powder (0.59 g, 55.9 mmol) was added slowly. This mixture stirred at room temp. for 72 h, then was diluted with water (25 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to give 5-(4-aminophenoxy)isoindoline-1,3-dione as a brownish solid (0.4 g, 75%): TLC (50% EtOAc/50% hexane) Rf0.27; 1H NMR (DMSO-d6) δ 5.14 (brs, 2H), 6.62 (d, J=8.7 Hz, 2H), 6.84 (d, J=8.7 Hz, 2H), 7.03 (d, J=2.1 Hz, 1H), 7.23 (dd, 1H), 7.75 (d, J=8.4 Hz, 1H), 11.02 (s, 1H); HPLC ES-MS m/z 255 ((M+H)+, 100%).

후처리

  1. additionwas added slowly
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1ed34b604d804445b16049420218e368
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528255B2

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