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

HRID 1704811Notes

Reaction equation

HRID 1704811 reaction equation
[O:1]=[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.[OH-].[Na+].O>C(O)C>[O:1]=[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 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 13851097Ethyl 4-Oxo-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 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (2.78 g., 0.010 mole), 1.0 N NaOH (15.0 ml.), H2O (40 ml.) and ethanol (30 ml.) was refluxed for 15 minutes. The mixture was filtered and the cooled filtrate acidified with 15.0 ml. of 1.0 N HCl to precipitate crude acid (2.36 g.), m.p. 193°-223°. Two recrystallizations from 2-methoxyethanol gave peach needles, m.p. 252°-253.5°.

Workup

  1. temperaturewas refluxed for 15 minutes
  2. filtrationThe mixture was filtered
  3. customof 1.0 N HCl to precipitate crude acid (2.36 g.), m.p. 193°-223°
  4. customTwo recrystallizations from 2-methoxyethanol
  5. customgave peach needles, m.p. 252°-253.5°

Sources & evidence

ORD record
ord-a59d824971bf4c57bb5dc76074e0fe98
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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