Diethyl (ethoxymethylene)malonate → HCID 13055793, compound

HRID 615426Notes

Reaction equation

HRID 615426 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]([CH3:12])[CH2:9][CH:8]([CH3:13])[NH:7]2.C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>O>[Cl:1][C:2]1[C:11]2[N:10]([CH3:12])[CH2:9][CH:8]([CH3:13])[N:7]3[CH:24]=[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17](=[O:16])[C:5]([C:6]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 13055792HCID 13055792, compound

Product 1

HCID 13055793HCID 13055793, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.0765 mole (15 g) of 8-chloro-1,3-dimethyl-1,2,3,4-tetrahydroquinoxaline and 0.0765 mole (16.5 g) of diethyl ethoxymethylenemalonate is heated under a nitrogen atmosphere at 145° to 150° C. for about 75 minutes. The solution is cooled, 70 g of polyphosphoric acid are added and the mixture is heated under nitrogen at 110° to 120° C. for 45 minutes. The hot solution is poured into water with stirring and a white solid precipitates. The product is recrystallized from ethanol to provide ethyl 10-chloro-2,3-dihydro-1,3-dimethyl-7-oxo-1H,7H-pyrido[1,2,3-de]quinoxaline-6-carboxylate, m.p. 259°-261° C. Analyis: Calculated for C16H17ClN2O3 : %C, 60.0, %H, 5.35; %H, 8.75; Found: %C, 60.0; %H, 5.3; %N, 8.9.

Workup

  1. temperatureis heated under a nitrogen atmosphere at 145° to 150° C. for about 75 minutes
  2. temperatureThe solution is cooled
  3. temperaturethe mixture is heated under nitrogen at 110° to 120° C. for 45 minutes
  4. customa white solid precipitates
  5. customThe product is recrystallized from ethanol

Sources & evidence

ORD record
ord-e4200c8f3e6c4bb5b342682348ea03fa
Source dataset
uspto-grants-1985_02
Patent number
US04499270

Reaction notes

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