Propylamine → Flavodilol

HRID 2291730ノート

反応式

HRID 2291730 の反応式
[CH2:1]([NH2:4])[CH2:2][CH3:3].[O:5]1[CH2:26][CH:6]1[CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:25])[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16]2)=[CH:11][CH:10]=1>C(O)C>[OH:5][CH:6]([CH2:26][NH:4][CH2:1][CH2:2][CH3:3])[CH2:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:25])[CH:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:16]2)=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 7852PropylamineHCID 99480817-(2,3-Epoxypropoxy)flavone

生成物 1

HCID 54410Flavodilol収率 57%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To 10.35 liters (125.9 mol) of n-propylamine were added 530 g (1.8 mol) of 7-(2,3-epoxypropoxy)flavone and 5.4 liters of abs ethanol. The mixture was heated at 50° to 55° for 1.5 hr, with stirring. The reaction mixture was cooled and clarified by filtration, and the filtrate concentrated in a rotary evaporator to a volume of 4.0 liters. The resulting solid product was filtered and washed with 1 liter abs ethanol; yield 383 g (60%) of a bright yellow solid, m.p. 144°-146°. The bright yellow solid was suspended in a mixture of 3.41 liters of water and 1.14 liters of 95% ethanol and then treated with 537 ml of 2.5N hydrochloric acid to obtain a solution of pH 1 to 2. The resulting aqueous solution was extracted twice with 537 ml of methylene chloride and then four times with 268 ml of CH2Cl2. The aqueous solution was clarified by filtration. Water (1.14 liters) was added to the filtrate, followed by the slow addition of 537 ml of 2.5N NaOH until the mixture tested for a pH of 10 to 11 to give a solid precipitate. The mixture was stirred for 1/2 hr. The product was filtered, washed with 2.68 liters water and air dried; yield, 362 g (57%) of the title compound as a pale yellow powder, m.p. 145°-147°.

後処理

  1. temperatureThe mixture was heated at 50° to 55° for 1.5 hr
  2. temperatureThe reaction mixture was cooled
  3. filtrationclarified by filtration
  4. concentrationthe filtrate concentrated in a rotary evaporator to a volume of 4.0 liters
  5. filtrationThe resulting solid product was filtered
  6. washwashed with 1 liter abs ethanol
  7. additionThe bright yellow solid was suspended in a mixture of 3.41 liters of water and 1.14 liters of 95% ethanol
  8. additiontreated with 537 ml of 2.5N hydrochloric acid
  9. customto obtain a solution of pH 1 to 2
  10. extractionThe resulting aqueous solution was extracted twice with 537 ml of methylene chloride
  11. filtrationThe aqueous solution was clarified by filtration
  12. additionWater (1.14 liters) was added to the filtrate
  13. additionfollowed by the slow addition of 537 ml of 2.5N NaOH until the mixture
  14. customto give a solid precipitate
  15. stirringThe mixture was stirred for 1/2 hr
  16. filtrationThe product was filtered
  17. washwashed with 2.68 liters water and air
  18. customdried
  19. customyield

出典と根拠

ORDレコード
ord-74da5d925a1a49778de3c949273f0ffb
出典データセット
uspto-grants-1989_01
特許番号
US04797498

反応ノート

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