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

HRID 15014

反応式

HRID 15014 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 882672-Methylphenethyl alcohol溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-54e07e9af4464f6988cfab1ed5303406
出典データセット
uspto-grants-2010_06
特許番号
US07732457B2

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