Ammonia → 6-(4-Methoxyphenyl)-4-oxo-4H-pyran-2-carboxamide

HRID 544154Notes

Reaction equation

HRID 544154 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:14][C:13]([C:15](OCC)=[O:16])=[CH:12][C:11](=[O:20])[CH:10]=2)=[CH:5][CH:4]=1.[NH3:21]>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:14][C:13]([C:15]([NH2:21])=[O:16])=[CH:12][C:11](=[O:20])[CH:10]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 12846663HCID 12846663, compound

Product 1

HCID 3429746-(4-Methoxyphenyl)-4-oxo-4H-pyran-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-(4-methoxyphenyl)-4-oxo-4H-pyran-2-carboxylate (27.4 g), ammonia solution (30%, 50 ml) and ethanol (300 ml) was heated under reflux for an hour. The yellow solid which precipitated on cooling was filtered off and recrystallised from acetic acid-ethanol to yield the title product (mp 303°-308° C. with decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for an hour
  3. customThe yellow solid which precipitated
  4. temperatureon cooling
  5. filtrationwas filtered off
  6. customrecrystallised from acetic acid-ethanol

Sources & evidence

ORD record
ord-3dfcc56ac6e241f8a88755fe5268cd44
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

Loading…