2,6-Dichlorobenzaldehyde → HCID 12818460, compound

HRID 2059089Notes

Reaction equation

HRID 2059089 reaction equation
[CH3:1][N:2]1[CH2:7][C:6](O)=[CH:5][C:4](=[O:9])[CH2:3]1.[Cl:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[C:12]=1[CH:13]=O.[CH3:20][O:21][C:22](=[O:27])/[CH:23]=[C:24](\[NH2:26])/[CH3:25]>C(O)C>[CH3:20][O:21][C:22]([C:23]1[CH:13]([C:12]2[C:11]([Cl:10])=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:19])[C:5]2[C:4](=[O:9])[CH2:3][N:2]([CH3:1])[CH2:7][C:6]=2[NH:26][C:24]=1[CH3:25])=[O:27]

Participants

5

Reactant 3

HCID 67372,6-DichlorobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 12818451HCID 12818451, compound

Product 1

HCID 12818460HCID 12818460, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7.25 g. of 1-methyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 8.75 g. of 2,6-dichlorobenzaldehyde, 5.94 g. of methyl-3-aminocrotonate (97%) and 135 ml. of ethanol were heated at reflux for 3 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was slurried with ethanol and the solid was separated by filtration. The solid, m.p. 258°-260° C. dec, was suspended in ethanol and saturated with hydrogen chloride. The solution was evaporated to dryness. The residue was triturated with a small volume of ethanol and filtered. The solid was recrystallized from 95% ethanol to obtain the title compound as the hydrochloride, m.p. 260°-262° C. dec.

Workup

  1. additionA mixture of 7.25 g
  2. temperatureat reflux for 3 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated to dryness
  5. customthe solid was separated by filtration
  6. customThe solution was evaporated to dryness
  7. customThe residue was triturated with a small volume of ethanol
  8. filtrationfiltered
  9. customThe solid was recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-11987de8482d44e98d780106ed7b29ff
Source dataset
uspto-grants-1982_03
Patent number
US04321384

Reaction notes

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