Diethyl (ethoxymethylene)malonate → HCID 22758830, compound

HRID 1704820Notes

Reaction equation

HRID 1704820 reaction equation
C(O[CH:4]=[C:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[CH2:20][CH2:19][N:18]=1>C1(C)C=CC=CC=1>[CH3:28][O:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[C:17]1=[N:16][CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11](=[O:13])[N:18]1[CH2:19][CH2:20]2

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 18785966HCID 18785966, compound

Product 1

HCID 22758830HCID 22758830, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diethyl ethoxymethylenemalonate (10.72 g., 0.0496 mole) was added to a stirred mixture at 25° of 1-amino-3,4-dihydro-6-methoxyisoquinoline (8.75 g., 0.0496 mole) in toluene (330 ml.). Stirring was continued for 10 minutes after which the temperature of the resulting yellow solution was raised to the reflux point during ten minutes. The solution was refluxed for 5 minutes and cooled to give ethyl 6,7-dihydro-9-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate, m.p. 158°-160° C. Successive recrystallizations from ethyl acetate and ethanol gave off-white flocculent needles: 10.3 g. (69% yield), m.p. 173°-175°.

Workup

  1. temperatureafter which the temperature of the resulting yellow solution was raised to the reflux point during ten minutes
  2. temperatureThe solution was refluxed for 5 minutes
  3. temperaturecooled

Sources & evidence

ORD record
ord-29f0205e36b943ebae891d2df3fc2fd7
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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