Ethanol → HCID 20081854, compound

HRID 1681252Notes

Reaction equation

HRID 1681252 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[NH2:19]/[C:20](/[CH3:26])=[CH:21]\[C:22]([O:24][CH3:25])=[O:23].C(O)C>C(O)(=O)C>[CH3:26][C:20]1[NH:19][C:10]([CH3:11])=[C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:21]=1[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 702EthanolHCID 643918Methyl 3-aminocrotonate3×HCID 53654424HCID 53654424, compound

Product 1

HCID 20081854HCID 20081854, compoundYield 111.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

24.0 g (0.1 mol) of 1-(4-fluorophenyl)-2-phenyl-buten-3-one, 23 g (0.2 mol) of methyl 3-amino-crotonate and 6 ml (0.1 mol) of glacial acetic acid are heated under reflux overnight in 150 m of ethanol, heated under reflux for 18 h after addition of 11.5 g (0.1 mol) of methyl 3-aminocrotonate and 3 ml of glacial acetic acid and heated under reflux for 18 h once more after repeated addition of 11.5 g (0.1 mol) of methyl 3-aminocrotonate and 3 ml of glacial acetic acid. The solvent is removed in vacuo, 80 ml of methanol are added to the residue, undissolved material is filtered off with suction, the methanolic solution is concentrated in vacuo and excess aminocrotonate is distilled off from the residue at 73° C.-90° C./18 mbar and subsequently at 60° C.-70° C. 0.2 mbar. 37.5 g of crude product are obtained as a brittle fused mass.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 18 h
  3. temperatureheated
  4. temperatureunder reflux for 18 h once more
  5. customThe solvent is removed in vacuo, 80 ml of methanol
  6. additionare added to the residue, undissolved material
  7. filtrationis filtered off with suction
  8. concentrationthe methanolic solution is concentrated in vacuo and excess aminocrotonate
  9. distillationis distilled off from the residue at 73° C.-90° C./18 mbar
  10. customsubsequently at 60° C.-70° C

Sources & evidence

ORD record
ord-2fe1433758994d61a725ccf54d891679
Source dataset
uspto-grants-1992_12
Patent number
US05169857

Reaction notes

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