Water → HCID 13533227, compound

HRID 2397585Notes

Reaction equation

HRID 2397585 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([C:15](=[O:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])[CH:9]=[CH:10][C:11]=2[O:13]C)[CH:6]=[CH:5][C:3]1=[O:4].O>Br>[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([C:15](=[O:21])[CH2:16][NH:17][CH:18]([CH3:19])[CH3:20])[CH:9]=[CH:10][C:11]=2[OH:13])[CH:6]=[CH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 962WaterHCID 21436084HCID 21436084, compound

Product 1

HCID 13533227HCID 13533227, compoundYield 23.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

2.0 g of 1-methyl-5-isopropylaminoacetyl-8-methoxycarbostyril (IIb) hydrochloride prepared as described in Example 3 was dissolved in 30 ml of a 47% aqueous solution of hydrobromic acid, and the solution was heated in an oil bath at a temperature of 120° to 130° C. for 8 hours under refluxing. 10 ml of water was then added to the reaction mixture followed by concentration by distillation. 10 ml of water was again added to the mixture followed by concentration. After allowing the mixture to cool, the precipitate formed was filtered and dissolved in 60 ml of water by heating. The resulting solution was adjusted to a pH of 6.5-7.5 with sodium bicarbonate and the precipitate formed was filtered. Recrystallization of the precipitate from ethanol yielded 0.45 g of white amorphous 1-methyl-5-isopropylaminoacetyl-8-hydroxycarbostyril (IIa) having a melting point of 136° to 138° C (with decomposition). The product thus obtained was confirmed by elemental analysis and IR and NMR spectral analyses.

Workup

  1. temperaturethe solution was heated in an oil bath at a temperature of 120° to 130° C. for 8 hours
  2. temperatureunder refluxing
  3. concentrationfollowed by concentration by distillation
  4. addition10 ml of water was again added to the mixture
  5. concentrationfollowed by concentration
  6. temperatureto cool
  7. customthe precipitate formed
  8. filtrationwas filtered
  9. dissolutiondissolved in 60 ml of water
  10. temperatureby heating
  11. customthe precipitate formed
  12. filtrationwas filtered
  13. customRecrystallization of the precipitate from ethanol

Sources & evidence

ORD record
ord-5f482dfbc76644f88ef895b8f3fafef7
Source dataset
uspto-grants-1977_05
Patent number
US04022784

Reaction notes

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