HCID 22758819, compound → HCID 22758848, compound

HRID 1704825Notes

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

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

  1. temperatureThe solution was cooled
  2. customthe yellow product collected
  3. washwashed with water
  4. dissolutiondissolved in warm 0.5 N NaOH (80 ml.)
  5. additionThe basic solution was treated with decolorizing carbon
  6. filtrationfiltered
  7. washThe precipitated material was washed on the
  8. filtrationfilter successively with water, ethanol and acetone
  9. customto give 3.5 g

Sources & evidence

ORD record
ord-6fffbd6068e443cca6013c423c7d7d63
Source dataset
uspto-grants-1978_11
Patent number
US04127720

Reaction notes

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