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

HRID 1283174Notes

Reaction equation

HRID 1283174 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 2 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 2 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-30c246cdc7be461280909eb2da7dabc5
Source dataset
uspto-grants-1976_08
Patent number
US03974161

Reaction notes

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