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

HRID 1902830

Reaction equation

HRID 1902830 reaction equation
[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

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 113598-AminoquinolineHCID 13140Acryloyl chloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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°).

Workup

  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

Sources & evidence

ORD record
ord-46fa04885f3f47d2a6a0eae34f4c812b
Source dataset
uspto-grants-1982_12
Patent number
US04366158

Linked notes

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