Phosphoric Acid → 7-methoxy-4-phenyl-quinolin-2-ol

HRID 1655021Notes

Reaction equation

HRID 1655021 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:20])[CH2:11][C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.OP(O)(O)=O>O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10](=[O:20])[NH:9]2)=[CH:7][CH:8]=1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:11][C:10](=[O:20])[NH:9]2

Participants

5

Reactant 2

HCID 1004Phosphoric AcidHCID 699437N-(3-methoxyphenyl)-3-oxo-3-phenylpropanamide

Product 2

HCID 7227187-methoxy-4-phenyl-quinolin-2-olHCID 20077466HCID 20077466, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of N-(3-methoxyphenyl)benzoylacetamide (5.8 g), o-phosphoric acid (30 mL of 85% acid in H2O) and H2O (30 mL) was heated at 100°-110° C. for 6 hr. After cooling to r.t., H2O (50 mL) was added and the precipitate that formed was collected by filtration. The title compound was thus obtained as a mixture with the regioisomeric product, 5-methoxy-4-phenyl-2-quinolinone, and used as such.

Workup

  1. temperaturewas heated at 100°-110° C. for 6 hr
  2. customthe precipitate that formed
  3. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-22709ec4a6c84e0f81ebe67a799bfd67
Source dataset
uspto-grants-1995_04
Patent number
US05410054

Reaction notes

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