Diethyl (ethoxymethylene)malonate → HCID 13606796, compound

HRID 652734Notes

Reaction equation

HRID 652734 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[C:5]([CH3:15])=[CH:4][N:3]=1.C([O:18][CH:19]=[C:20]([C:26](OCC)=O)[C:21]([O:23][CH2:24][CH3:25])=[O:22])C>CN(C)C=O>[CH3:15][C:5]1[C:6]2[C:11](=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=2)[C:2]2=[N:1][CH:26]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](=[O:18])[N:3]2[CH:4]=1

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonate2×HCID 13606795HCID 13606795, compound

Product 1

HCID 13606796HCID 13606796, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-amino-4-methyl-7-nitroisoquinoline (3.87 g), diethyl ethoxymethylenemalonate (4.53 g) in N,N-dimethylformamide (20 ml) was heated at 120° C. with stirring for 4 hours. Additional diethyl ethoxymethylenemalonate (1 g) was added to the mixture, and then the reaction mixture was refluxed for 18 hours and cooled to give precipitate. The crystals obtained were filtered off and washed with cold ethanol to give ethyl 7-methyl-10-nitro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (4.21 g).

Workup

  1. temperaturethe reaction mixture was refluxed for 18 hours
  2. temperaturecooled
  3. customto give precipitate
  4. customThe crystals obtained
  5. filtrationwere filtered off
  6. washwashed with cold ethanol

Sources & evidence

ORD record
ord-de79ad1dd67f42529390bb413611f7f0
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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