Pyrrolidine → Pyridazino(4,3-c)isoquinoline, 3-phenyl-6-(1-pyrrolidinyl)-

HRID 986751Notes

Reaction equation

HRID 986751 reaction equation
[C:1]1([C:7]2[N:20]=[N:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[CH:11]=[N:10][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C(COC)OC>[C:1]1([C:7]2[N:20]=[N:19][C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[C:11]([N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:10][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 13526643HCID 13526643, compound

Product 1

HCID 13526627Pyridazino(4,3-c)isoquinoline, 3-phenyl-6-(1-pyrrolidinyl)-Yield 93.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

3-Phenyl-pyridazino-[4,3-c]isoquinoline (5.83 g, 0.02 mol) and dimethoxyethane (100 ml) are heated to reflux temperature with stirring in a 250 ml flask. Pyrrolidine (3.1 g, 0.044 mol) is added to the obtained solution and heating is continued for further 2 hours. When the reaction is completed, the reaction mixture is concentrated to dryness under reduced pressure and the residue is taken up with water (200 ml), a solid is recovered by filtrating the obtained suspension which is dried yielding 6.1 g of a crude 3-phenyl-6-(1-pyrrolidinyl)pyridazino[4,3-c]isoquinoline. Crystallization from ethyl acetate gives 5.6 g of the pure product of the title. (Yield 85%) M.p. 174°-176° C.

Workup

  1. temperatureto reflux temperature
  2. temperatureheating
  3. concentrationthe reaction mixture is concentrated to dryness under reduced pressure
  4. customa solid is recovered
  5. filtrationby filtrating the obtained suspension which
  6. customis dried

Sources & evidence

ORD record
ord-b3dcad93cd154d6a8f4e97500d7d7844
Source dataset
uspto-grants-1987_12
Patent number
US04716159

Reaction notes

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