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Water → 4,4'-(1-(4-Fluorophenyl)-1H-pyrrole-2,5-diyl)dianiline

HRID 1470917
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HRID 1470917 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=3)=[CH:11][CH:10]=[C:9]2[C:22]2[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[Cl-].[NH4+].O>C(O)C.C1COCC1.[Fe]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:9]([C:22]3[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=3)=[CH:10][CH:11]=[C:12]2[C:13]2[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 582268151-(4-Fluorophenyl)-2,5-bis(4-nitrophenyl)-1H-pyrrole

생성물 1

HCID 582267494,4'-(1-(4-Fluorophenyl)-1H-pyrrole-2,5-diyl)dianiline수율 127.2%

시약·촉매·용매 3

HCID 23925Iron촉매HCID 702
Ethanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of example 19A (1.017 g, 2.496 mmol) in ethanol (15 mL) and THF (15 mL) was added iron powder (0.836 g, 14.98 mmol) followed by ammonium chloride (0.401 g, 7.49 mmol) and water (3.75 mL). Reaction mixture was refluxed for 45 minutes. Slurry filtered through celite, washed with ethanol, combined filtrate was concentrated and the residue purified by column chromatography (gradient elution from 30% to 50% EtOAc:hexanes) to provide 1.09 g (77%) of the title compound.

후처리

  1. customReaction mixture
  2. temperaturewas refluxed for 45 minutes
  3. filtrationSlurry filtered through celite
  4. washwashed with ethanol
  5. concentrationwas concentrated
  6. customthe residue purified by column chromatography (gradient elution from 30% to 50% EtOAc:hexanes)

출처 및 근거

ORD 기록
ord-b0e80b23588c489bbae9f94a728d6c3d
출처 데이터셋
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09006387B2

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