Acetic Acid → 4-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic Acid

HRID 1704813Notes

Reaction equation

HRID 1704813 reaction equation
N=[C:2]1[N:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=[C:3]1[C:16]([O:18]CC)=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3.C(O)(=[O:23])C>Cl.O>[O:23]=[C:2]1[N:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]2=[N:5][CH:4]=[C:3]1[C:16]([OH:18])=[O:17])=[CH:14][CH:13]=[CH:12][CH:11]=3

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22758844ethyl 4-imino-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

Product 1

HCID 227588274-Oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic Acid

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 4-imino-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (1.0 g.) in acetic acid (20 ml.) and 37% hydrochloric acid (20 ml.) was refluxed for 35 minutes. The solution was cooled and diluted with H2O to precipitate the crude acid (760 mg.), m.p. 219°-231° (prior softening). Recrystallized material (2-methoxyethanol) and a m.p. of 249°-252° and mixed melting point of 252°-255° with product from Example 2.

Workup

  1. temperatureThe solution was cooled
  2. customto precipitate the crude acid (760 mg.), m.p. 219°-231° (prior softening)
  3. additionRecrystallized material (2-methoxyethanol) and a m.p. of 249°-252° and mixed melting point of 252°-255° with product from Example 2

Sources & evidence

ORD record
ord-c73e0f591eed410db64987fb6f9e5957
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

Loading…