Acetic Acid → (E)-N-[2-(3,4-dimethoxyphenyl)-2-(hydroxyimino)ethyl]-N-methyl-3-(3-pyridyl)-2-propenamide

HRID 428140ノート

反応式

HRID 428140 の反応式
C(O)(=O)C.[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=O)[CH2:16][N:17]([CH3:28])[C:18](=[O:27])/[CH:19]=[CH:20]/[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14].[NH2:30][OH:31].O>CCCCCC.C(OCC)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:15](=[N:30][OH:31])[CH2:16][N:17]([CH3:28])[C:18](=[O:27])/[CH:19]=[CH:20]/[C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH3:14]

参加物

7

反応物 4

HCID 176Acetic Acid2 回HCID 787HydroxylamineHCID 962WaterHCID 20701373(E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamide

生成物 1

HCID 60029022(E)-N-[2-(3,4-dimethoxyphenyl)-2-(hydroxyimino)ethyl]-N-methyl-3-(3-pyridyl)-2-propenamide収率 51.2%

試薬・触媒・溶媒 2

HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Acetic acid (3 ml) was added to (E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenoic acid amide (165 mg, 0.5 mmol) and allowed to stand at −20° C. After acetic acid was solidified, 50% aqueous hydroxylamine solution (0.62 ml, 10 mmol) was added under ice-cooling and reacted at the same temperature. After warming to room temperature and reacting for further 22 hours, water (10 ml) and ethyl acetate (10 ml) were added and extracted three times with ethyl acetate (10 ml). The organic layer was washed sequentially with water (40 ml) and aqueous saturated sodium chloride solution (40 ml) and dried over anhydrous magnesium sulfate (10 g). The drying agent was removed out and the filtrate was concentrated. The resulting dry product was purified by a column chromatography using silica gel (20 g) (elution with dichloromethane: methanol=100:3.5). After purification, the product was recrystallized in ethyl acetate (5 ml) and n-hexane (15 ml) to yield the titled compound (91 mg, yield 51%).

後処理

  1. customto stand at −20° C
  2. temperaturecooling
  3. customreacted at the same temperature
  4. extractionextracted three times with ethyl acetate (10 ml)
  5. washThe organic layer was washed sequentially with water (40 ml) and aqueous saturated sodium chloride solution (40 ml)
  6. dry with materialdried over anhydrous magnesium sulfate (10 g)
  7. customThe drying agent was removed out
  8. concentrationthe filtrate was concentrated
  9. customThe resulting dry product was purified by a column chromatography
  10. customAfter purification
  11. customthe product was recrystallized in ethyl acetate (5 ml)

出典と根拠

ORDレコード
ord-e4d7039c0cb34c8a9bbed53c06c9f0bf
出典データセット
uspto-grants-2001_11
特許番号
US06313153B1

反応ノート

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