Sodium Carbonate → 4-(4'-Cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acid

HRID 381844ノート

反応式

HRID 381844 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=O)[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].Cl.[NH2:23][OH:24].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15](=[N:23][OH:24])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 183641364-(4'-Cyano-biphenyl-4-yl)-4-oxo-butyric acid

生成物 1

HCID 734323184-(4'-Cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acid収率 49.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A stirred suspension of 4-(4′-cyano-biphenyl-4-yl)-4-oxo-butyric acid (0.7908 g, 0.002831 mol), hydroxylamine hydrochloride (0.2038 g, 0.00293 mol), sodium carbonate (0.3158 g, 0.00298 mol) in absolute ethanol (17 mL) was refluxed under nitrogen for 12 hours and allowed to cool. The mixture was allowed to stand for 2.5 days for convenience. Volatiles were rotary evaporated, and the residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.05 M aqueous hydrochloric acid (60 mL). The aqueous layer was extracted with additional organics. The extracts were combined, dried (Na2SO4) and rotary evaporated. The residue was dissolved/suspended in dichloromethane and chromatographed on silica gel (165 g, 230-400 mesh), eluting with dichloromethane-methanol (25:1, 30×125 mL; 15:1, 5×125 mL) to give 0.413 g of 4-(4′-cyano-biphenyl-4-yl)-4-hydroxyimino-butyric acid as an off-white solid; mp 157-159° C.

後処理

  1. temperaturewas refluxed under nitrogen for 12 hours
  2. temperatureto cool
  3. customthe residue was partitioned between dichloromethane-tetrahydrofuran (50/50 v/v) and 0.05 M aqueous hydrochloric acid (60 mL)
  4. extractionThe aqueous layer was extracted with additional organics
  5. dry with materialdried (Na2SO4) and rotary evaporated
  6. customchromatographed on silica gel (165 g, 230-400 mesh)
  7. washeluting with dichloromethane-methanol (25:1, 30×125 mL; 15:1, 5×125 mL)

出典と根拠

ORDレコード
ord-28cc515eac2743389b7541b88afc71e3
出典データセット
uspto-grants-2001_10
特許番号
US06307089B2

反応ノート

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