Water → 2-Propenoic acid, 2-(acetylamino)-3-(3-pyridinyl)-, (2Z)-

HRID 27218

反応式

HRID 27218 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([NH:12][CH2:13][C:14]([OH:16])=[O:15])(=[O:11])[CH3:10].C([O-])(=O)C.[Na+].O>C(OC(=O)C)(=O)C.CC(C)=O>[C:9]([NH:12][C:13](=[CH:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:14]([OH:16])=[O:15])(=[O:11])[CH3:10]

参加物

7

反応物 4

HCID 962Water2 回HCID 103713-PyridinecarboxaldehydeHCID 10972AcetylglycineHCID 517045Sodium Acetate

生成物 1

HCID 44389982-Propenoic acid, 2-(acetylamino)-3-(3-pyridinyl)-, (2Z)-収率 23.1%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 7918Acetic Anhydride溶媒

実験手順

Pyridine-3-carboxaldehyde (92.6 g), N-acetylglycine (86.0 g) and sodium acetate (35.3 g) were heated together under reflux in acetic anhydride (150 ml) for 1 hour. After cooling, water (250 ml) was added and the mixture was filtered to give the crude azlactone (50.9 g) m.p. 55°-60°. Partial hydrolysis of the azlactone (50 g) was achieved by heating under reflux in acetone (450 ml) and water (75 ml) for four hours. After this time the bulk of the acetone was distilled off and more water (300 ml) added. The resulting deep red solution was boiled with charcoal for 10 minutes and filtered through celite. The filtrate was evaporated to dryness and the residue was triturated and washed with acetone to give 2-acetamido-3-(3-pyridyl)acrylic acid (35 g) m.p. 191°-92° which was not further purified.

後処理

  1. temperatureAfter cooling
  2. filtrationthe mixture was filtered
  3. customto give the crude azlactone (50.9 g) m.p. 55°-60°
  4. temperatureby heating
  5. distillationAfter this time the bulk of the acetone was distilled off
  6. additionmore water (300 ml) added
  7. filtrationfiltered through celite
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was triturated
  10. washwashed with acetone

出典と根拠

ORDレコード
ord-1a09a5cde63a46b9a769fdc4c2dd476b
出典データセット
uspto-grants-1980_09
特許番号
US04220767

関連ノート

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