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Imidazole → 5-Amino-6-nitro-2-(pyridine-3-yl)isoindoline-1,3-dione

HRID 920471
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HRID 920471 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[NH:6][C:5]2=[O:15].N[C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1.N1C=CN=C1>C1(OC2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:7](=[O:14])[N:6]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:5]2=[O:15]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 100093-AminopyridineHCID 151445685-Amino-6-nitro-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 666871505-Amino-6-nitro-2-(pyridine-3-yl)isoindoline-1,3-dione수율 62.2%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
190 °C

실험 절차

5-Amino-6-nitroisoindoline-1,3-dione (3.00 g, 14.48 mmol), 3-aminopyridine (5.45 g, 57.92 mmol) and imidazole (3.94 g, 57.92 mmol) were suspended in diphenyl ether (50 mL). The mixture was stirred and heated to 190° C. for 3 days under argon. Then, the solid was filtered, washed with hexanes and purified by column chromatography (silica-gel, CH2Cl2/Acetone=7/3 v/v) to give a yellow solid product, 2.56 g, 62.2% yield. MS: 282.8 [M−H]−. 1H NMR (DMSO-d6, 500 MHz): δ 8.65 (d, 1H, J=2.0 Hz), 8.62 (dd, 1H, J1=5.0 Hz, J2=1.0 Hz), 8.46 (S, 2H), 8.42 (s, 1H), 7.89 (m, 1H), 7.60-7.58 (m, 1H), 7.55 (s, 1H).

후처리

  1. filtrationThen, the solid was filtered
  2. washwashed with hexanes
  3. custompurified by column chromatography (silica-gel, CH2Cl2/Acetone=7/3 v/v)
  4. customto give a yellow solid product, 2.56 g, 62.2% yield

출처 및 근거

ORD 기록
ord-23b2ab0b757340819e32f15a923a6b0e
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273055B2

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