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HCID 22758819, compound → HCID 22758848, compound

HRID 1704825
Notes
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Reaction equation

HRID 1704825 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]3[C:16](=[O:17])[C:15]([C:18]([O:20]CC)=[O:19])=[CH:14][N:13]=[C:10]32)=[CH:5][CH:4]=1>Br>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]3[C:16](=[O:17])[C:15]([C:18]([OH:20])=[O:19])=[CH:14][N:13]=[C:10]32)=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 22758819HCID 22758819, compound

Product 1

HCID 22758848HCID 22758848, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of ethyl 6,7-dihydro-10-methoxy-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (5.0 g., 0.0175 mole) in 48% hydrobromic acid (125 ml.) was refluxed for 4 hours. The solution was cooled and the yellow product collected, washed with water, and dissolved in warm 0.5 N NaOH (80 ml.). The basic solution was treated with decolorizing carbon, filtered and the filtrate acidified with hydrochloric acid. The precipitated material was washed on the filter successively with water, ethanol and acetone to give 3.5 g. (81% yield) of the title acid, m.p. 326°-327°.

Workup

  • temperatureThe solution was cooled
  • customthe yellow product collected
  • washwashed with water
  • dissolutiondissolved in warm 0.5 N NaOH (80 ml.)
  • additionThe basic solution was treated with decolorizing carbon
  • filtrationfiltered
  • washThe precipitated material was washed on the
  • filtrationfilter successively with water, ethanol and acetone
  • customto give 3.5 g
  • Sources & evidence

    ORD record
    ord-6fffbd6068e443cca6013c423c7d7d63
    Source dataset
    uspto-grants-1978_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US04127720

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes