Ethanol → HCID 12818452, compound

HRID 2059086Notes

Reaction equation

HRID 2059086 reaction equation
[CH3:1][N:2]1[CH2:7][C:6](O)=[CH:5][C:4](=[O:9])[CH2:3]1.[C:10]1([CH3:18])[C:11]([CH:16]=O)=[CH:12][CH:13]=[CH:14][CH:15]=1.[CH3:19][O:20][C:21](=[O:26])/[CH:22]=[C:23](\[NH2:25])/[CH3:24].C(O)C>C(O)(=O)C>[CH3:19][O:20][C:21]([C:22]1[CH:16]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[CH3:18])[C:5]2[C:4](=[O:9])[CH2:3][N:2]([CH3:1])[CH2:7][C:6]=2[NH:25][C:23]=1[CH3:24])=[O:26]

Participants

6

Reactant 4

HCID 702EthanolHCID 107222-MethylbenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 12818451HCID 12818451, compound

Product 1

HCID 12818452HCID 12818452, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 7.65 g. of 1-methyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 7.2 g. of o-tolualdehyde, 6.9 g. of methyl-3-aminocrotonate (97%), 110 ml. of ethanol and 35 ml. of acetic acid was refluxed for 3 hours. The mixture was evaporated to dryness in vacuo. The residue was dissolved in dichloromethane and extracted with saturated sodium carbonate solution. The dichloromethane solution was evaporated to dryness. The residue was slurried with diethyl ether and the solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 249°-252° C. dec.

Workup

  1. additionA mixture of 7.65 g
  2. customThe mixture was evaporated to dryness in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. extractionextracted with saturated sodium carbonate solution
  5. customThe dichloromethane solution was evaporated to dryness
  6. customthe solid was separated by filtration
  7. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e456ae8f1f4e411d9299d95e4cb52556
Source dataset
uspto-grants-1982_03
Patent number
US04321384

Reaction notes

Loading…