Pyridine → HCID 178450503, compound

HRID 1885191Notes

Reaction equation

HRID 1885191 reaction equation
[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[O:21][CH3:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[C:1]([C:6](=[CH:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:29](=[O:36])[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:16][C:15]=1[O:21][CH3:22])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 178450500HCID 178450500, compound

Product 1

HCID 178450503HCID 178450503, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Ethyl 2-butyryl-3-(4-hydroxy-2-methoxyphenylamino)acrylate (34.5 g) and pyridine (100 ml) were stirred in dichloromethane (500 ml) at 0°-5°. Benzoyl chloride (20 ml) in dichloromethane (100 ml) was added dropwise (below 10°) and the mixture was stirred overnight at room temperature. The reaction mixture was washed successively with water, 2M HCl (×2) and sodium hydrogen carbonate solution (×2). The organic layer was dried, filtered and evaporated to an oil which crystallized on standing to give ethyl 2-butyryl-3-(4-benzoyloxy-2-methoxyphenyl-amino)acrylate (24 g, 52%) m.p. 85°-87°.

Workup

  1. washThe reaction mixture was washed successively with water, 2M HCl (×2) and sodium hydrogen carbonate solution (×2)
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customevaporated to an oil which
  5. customcrystallized

Sources & evidence

ORD record
ord-f88cf76092fa41dfb4e4fd40cd8ff096
Source dataset
uspto-grants-1992_09
Patent number
US05143920

Reaction notes

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