Acetic Acid → HCID 22758871, compound

HRID 1704822Notes

Reaction equation

HRID 1704822 reaction equation
[CH2:1]([CH:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C:7]2=[N:16][CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](=[O:20])[N:6]2[CH2:5]1)[CH:2]=[CH2:3].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH3:15])=[CH:11][CH:12]=2)[C:7]2=[N:16][CH:17]=[C:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:19](=[O:20])[N:6]2[CH:5]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22758847HCID 22758847, compound

Product 1

HCID 22758871HCID 22758871, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of ethyl 7-allyl-6,7-dihydro-10-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (1.5 g., 4.41 mmoles) and DDQ (1.1 g., 4.85 mmoles) in toluene (30 ml.) containing acetic acid (0.05 ml.) was refluxed for 18 hours. The mixture was filtered and the filtrate concentrated to dryness. Trituration of the residue with methanol gave a solid which was recrystallized from ethanol to give 201 mgs. of brown crystals, m.p. 182°-186°. The methanol mother liquor was concentrated to dryness and the residue chromatographed on silicic acid with toluene-acetone (20:1) to give additional product (230 mgs.), m.p. 177°-183° after recrystallization from ethanol. The material with m.p. 182°-186° was chromatographed in a similar manner and the product so obtained combined with the material with m.p. 177°-183° and the lot recrystallized from ethanol to give yellow needles of the title compound, m.p. 187°-188°.

Workup

  1. temperaturewas refluxed for 18 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated to dryness
  4. customTrituration of the residue with methanol gave a solid which
  5. customwas recrystallized from ethanol
  6. customto give 201 mgs
  7. concentrationThe methanol mother liquor was concentrated to dryness
  8. customthe residue chromatographed on silicic acid with toluene-acetone (20:1)
  9. customto give additional product (230 mgs.), m.p. 177°-183°
  10. customafter recrystallization from ethanol
  11. customThe material with m.p. 182°-186° was chromatographed in a similar manner
  12. customthe product so obtained
  13. customthe lot recrystallized from ethanol

Sources & evidence

ORD record
ord-ab0128b174d8477f9e13d3f89ab641b9
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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