HCID 178459173, compound → HCID 10036866, compound

HRID 1647486Notes

Reaction equation

HRID 1647486 reaction equation
[C:1]([C:5](=[CH:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[C:6]([O:8]C)=O)(=[O:4])[CH2:2][CH3:3]>C1(OC2C=CC=CC=2)C=CC=CC=1>[C:1]([C:5]1[C:6](=[O:8])[C:17]2[C:12](=[C:13]([O:18][CH3:19])[CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)(=[O:4])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 178459173HCID 178459173, compound

Product 1

HCID 10036866HCID 10036866, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent

Procedure

Methyl 2-propanoyl-3-(2-methoxyphenylamino)acrylate (77.7 g, 0.29 mol) was added to boiling diphenyl ether (500 ml) then heated at reflux for 1 hour. The solution was partially cooled and poured into high-boiling petroleum ether, then the solid filtered off and washed with 40-60 petroleum ether to give 3-propanoyl-8-methoxy-4(1H)-quinolone (35.6 g, 52%), m.p. 260°-263°

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 1 hour
  3. temperatureThe solution was partially cooled
  4. filtrationthe solid filtered off
  5. washwashed with 40-60 petroleum ether

Sources & evidence

ORD record
ord-d0a02e163c984a1f941938ec04f99ff6
Source dataset
uspto-grants-1995_07
Patent number
US05432182

Reaction notes

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