HCID 22758817, compound → HCID 22758834, compound

HRID 1704831Notes

Reaction equation

HRID 1704831 reaction equation
[CH2:1]([CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][CH:14]=[C:15]([C:18]#[N:19])[C:16](=[O:17])[N:5]2[CH2:4]1)[CH3:2]>[Pd].CC1C=CC(C(C)C)=CC=1.C(Cl)Cl>[CH2:1]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2=[N:13][CH:14]=[C:15]([C:18]#[N:19])[C:16](=[O:17])[N:5]2[CH:4]=1)[CH3:2]

Participants

5

Reactant 1

HCID 22758817HCID 22758817, compound

Product 1

HCID 22758834HCID 22758834, compoundYield 46%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 7463P-CymeneSolvent

Procedure

A stirred mixture of (±)-7-ethyl-6,7-dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carbonitrile (3.5 g.) and 10% palladium on carbon (1.5 g.) in p-cymene (50 ml.) was refluxed for 18 hours. The mixture was diluted with methylene chloride and filtered to remove the catalyst. The solvents were removed on a rotary evaporator and the residue crystallized from ethanol to give 1.6 g. (46% yield) of the title compound, m.p. 208°-211°. Successive recrystallizations from toluene and ethanol provided the analytical sample, m.p. 218°-219°.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationfiltered
  3. customto remove the catalyst
  4. customThe solvents were removed on a rotary evaporator
  5. customthe residue crystallized from ethanol
  6. customto give 1.6 g

Sources & evidence

ORD record
ord-92d5bbb314e14bf7acd0f4bad5822cf2
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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