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p-Toluenesulfonic acid → 2-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol

HRID 15014
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HRID 15014 반응식
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH2:13][CH2:14][O:15]C(=O)C)=[CH:5][CH:4]=1.[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26](=O)[CH2:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH3:40])=[CH:33][CH:32]=1)=O.CC1C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl>C1(C)C(CCO)=CC=CC=1>[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[N:1]([CH2:2][C:3]2[N:8]=[C:7]([N+:9]([O-:11])=[O:10])[C:6]([O:12][CH2:13][CH2:14][OH:15])=[CH:5][CH:4]=2)[C:29]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH3:40])=[CH:33][CH:32]=2)=[CH:28][CH:27]=1
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참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 6212ChloroformHCID 160903391-(2-Chlorophenyl)-4-(4-propoxyphenyl)-butane-1,4-dioneHCID 59341182Acetic acid 2-(6-aminomethyl-2-nitropyridin-3-yloxy)-ethyl ester

생성물 1

HCID 593412002-{6-[2-(2-Chlorophenyl)-5-(4-propoxyphenyl)-pyrrol-1ylmethyl]-2-nitro-pyridin-3-yloxy}-ethanol수율 32.6%

시약·촉매·용매

1
HCID 882672-Methylphenethyl alcohol용매

반응 조건

온도
100 °C

실험 절차

To a solution of 0.2 gm of acetic acid 2-(6-aminomethyl-2-nitropyridin-3-yloxy)-ethyl ester (0.8 mmol) in 3 mL of 5:1 toluene-ethanol was added 0.20 gm of 1-(2-chlorophenyl)-4-(4-propoxyphenyl)-butane-1,4-dione and 10 mg of p-TsOH. The reaction mixture stirred at 100° C. for 72 h. The reaction mixture was poured into 200 mL of CHCl3 and washed twice with water (100 mL), saturated brine, dried (Na2SO4), and the solvents removed under reduced pressure. The residue was purified by column chromatography using 4% methanol-chloroform as an eluent to give 100 mg (25% yield) of an oil. This was used without further purification or characterization.

후처리

  1. washwashed twice with water (100 mL), saturated brine
  2. dry with materialdried (Na2SO4)
  3. customthe solvents removed under reduced pressure
  4. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-54e07e9af4464f6988cfab1ed5303406
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07732457B2

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