Ethyl 2-aminobenzoate → (2,4-Dihydroxyquinolin-3-yl)(3,4-dimethoxyphenyl)methanone

HRID 370465Notes

Reaction equation

HRID 370465 reaction equation
[C:1]([O:10]CC)(=O)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:18]([CH2:20][C:21](OCC)=[O:22])=[O:19].[O-]CC.[Na+]>C1(C)C(C)=CC=CC=1>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:18]([C:20]1[C:21](=[O:22])[NH:4][C:3]2[C:2]([C:1]=1[OH:10])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:19]

Participants

5

Reactant 3

HCID 6877Ethyl 2-aminobenzoateHCID 2723922Sodium ethoxideHCID 2758465Ethyl 3,4-dimethoxybenzoylacetate

Product 1

HCID 135687071(2,4-Dihydroxyquinolin-3-yl)(3,4-dimethoxyphenyl)methanoneYield 17.6%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Ethyl anthranilate (1.44 grams) and 2.2 grams of ethyl 3,4-dimethoxybenzoylacetate are dissolved in 100 ml of xylene and heated to reflux for five hours with 200 mg of sodium ethoxide. After cooling, crystals are separated out and collected by filtration and recrystallized from methanol to give 0.5 grams of 3-(3,4-dimethoxybenzoyl)-4-hydroxy-2-quinolone, pale yellow needles, melting point 235° to 236° C.

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. customcrystals are separated out
  4. filtrationcollected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-4f5df185039743629473366af5d0b8c1
Source dataset
uspto-grants-1985_07
Patent number
US04526894

Reaction notes

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