Diethyl Oxalate → Ethyl benzo[g]quinazolin-4(3H)-one-2-carboxylate

HRID 442220Notes

Reaction equation

HRID 442220 reaction equation
[C:1]([O:8][CH2:9][CH3:10])(=[O:7])[C:2](OCC)=O.C[O-].[Na+].[NH2:14][C:15]1[C:24]([C:25]([NH2:27])=[O:26])=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=1>>[N:14]1[C:15]2[C:24](=[CH:23][C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[CH:16]=2)[C:25](=[O:26])[NH:27][C:2]=1[C:1]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 7268Diethyl OxalateHCID 10942334Sodium MethoxideHCID 124714773-aMino-2-naphthaMide

Product 1

HCID 135961510Ethyl benzo[g]quinazolin-4(3H)-one-2-carboxylateYield 79%

Procedure

Diethyl oxalate (2.35 g., 16.1 millimoles), sodium methoxide (10 mg) and 2-aminonaphthalene-3-carboxamide (1.50 g., 8.05 millimoles) are mixed together and heated at reflux for two days. The mixture is then cooled in an ice bath and the brown precipitate recovered by filtration. It is recrystallized from ethanol to give 1.76 g. (79% yield) of the desired ester. M.P. 240°-242° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for two days
  3. temperatureThe mixture is then cooled in an ice bath
  4. filtrationthe brown precipitate recovered by filtration
  5. customIt is recrystallized from ethanol
  6. customto give 1.76 g

Sources & evidence

ORD record
ord-d287f2122eb64eb7a2dc12855beccfa1
Source dataset
uspto-grants-1977_08
Patent number
US04044134

Reaction notes

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