Triethylamine → N-(8-quinolyl)-2-propenamide

HRID 1902830

反応式

HRID 1902830 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.C(N(CC)CC)C.[C:19](Cl)(=[O:22])[CH:20]=[CH2:21]>O1CCCC1>[N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[NH:1][C:19](=[O:22])[CH:20]=[CH2:21])[CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 13140Acryloyl chloride

生成物 1

HCID 12898545N-(8-quinolyl)-2-propenamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 8-aminoquinoline (14.4 g, 0.1 mole) and triethylamine (15 ml, 0.11 mole) in dry tetrahydrofuran (50 ml) was treated dropwise at 0° (under a nitrogen atmosphere) with a solution of acryloyl chloride (8.5 ml, 0.1 mole) in tetrahydrofuran (25 ml). The reaction was filtered and the filtrate was partitioned between methylene chloride and water. The organic phase was separated, dried over sodium sulphate and concentrated to an oil. The oil was dissolved in ethyl acetate, treated with charcoal, filtered and again concentrated by vacuum distillation to an oil. Seed crystals were added and the oil cooled to -18°. The solid mass was stirred with petroleum ether and filtered affording 15.7 g of crude product of sufficient purity for further synthetic steps. Recrystallization from acetone/pentane afforded N-(8-quinolyl)-2-propenamide of analytical purity (m.p. 76.5°-78.5°).

後処理

  1. filtrationThe reaction was filtered
  2. customthe filtrate was partitioned between methylene chloride and water
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated to an oil
  6. dissolutionThe oil was dissolved in ethyl acetate
  7. additiontreated with charcoal
  8. filtrationfiltered
  9. concentrationagain concentrated by vacuum distillation to an oil
  10. additionSeed crystals were added
  11. temperaturethe oil cooled to -18°
  12. filtrationfiltered
  13. customaffording 15.7 g of crude product of sufficient purity for further synthetic steps
  14. customRecrystallization from acetone/pentane

出典と根拠

ORDレコード
ord-46fa04885f3f47d2a6a0eae34f4c812b
出典データセット
uspto-grants-1982_12
特許番号
US04366158

関連ノート

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