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Ammonium Chloride → 4'-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

HRID 1617507
ノート
印刷プレビュー

反応式

HRID 1617507 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=O)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)=[O:4].Cl.[NH2:36][OH:37].C(=O)([O-])O.[Na+].[NH4+].[Cl-]>C(O)C.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:12]=[CH:13][C:14]([CH:17]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[CH2:18][C:19](=[N:36][OH:37])[C:21]3[CH:26]=[CH:25][N:24]=[C:23]([CH3:27])[CH:22]=3)=[CH:15][CH:16]=2)=[CH:9][CH:10]=1)=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 666667824'-[3-(2-Methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

生成物 1

HCID 1363599834'-[3-[Hydroxyimino]-3-(2-methyl-pyridin-4-yl)-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of 4′-[3-(2-methyl-pyridin-4-yl)-3-oxo-1-o-tolyl-propyl]-biphenyl-4-carboxylic acid methyl ester (36 mg), hydroxylamine hydrochloride (11 mg) and sodium hydrogencarbonate (14 mg) in a mixture of ethanol (0.5 mL) and water (0.1 mL) was heated under reflux for 1.5 hours. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1) to yield the title compound as a mixture of E and Z isomers (3.3:1) as a white foam (28 mg, 75%), MS (ESI+): m/z=465.2 ([M+H]+).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 2:1)

出典と根拠

ORDレコード
ord-8bc1d4edea4148e598b3435d0886c219
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08765730B2

反応ノート

読み込み中…

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