Hydrochloric Acid → 6,7-Dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic Acid

HRID 1704818Notes

Reaction equation

HRID 1704818 reaction equation
[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][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+].Cl>C(O)C>[O:1]=[C:2]1[N:7]2[CH2:8][CH2:9][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 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22758857Ethyl 6,7-Dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate

Product 1

HCID 227588156,7-Dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic AcidYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6,7-dihydro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (1.81 g., 6.7 mmoles), 1.0 N NaOH (25 ml.) and 95% ethanol was refluxed for 20 l minutes. The resulting solution was cooled and acidified with 1.0 HCl (26 ml.) to precipitate the acid, which was crystallized from 2-methoxyethanol to give colorless crystals: 1.02 g. (63% yield), m.p. 215°-217°. An additional recrystallization from 2-methoxyethanol gave material with m.p. 215.5°-217°.

Workup

  1. temperaturewas refluxed for 20 l minutes
  2. temperatureThe resulting solution was cooled
  3. customto precipitate the acid, which
  4. customwas crystallized from 2-methoxyethanol
  5. customto give colorless crystals
  6. customAn additional recrystallization from 2-methoxyethanol
  7. customgave material with m.p. 215.5°-217°

Sources & evidence

ORD record
ord-e174cd4e7cf64a32adb97b31105e30bd
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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