5-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one → HCID 13533227, compound

HRID 2397584Notes

Reaction equation

HRID 2397584 reaction equation
[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([C:15](=[O:18])[CH2:16]Cl)[CH:9]=[CH:10][C:11]=2[O:13]C)[CH:6]=[CH:5][C:3]1=[O:4]>CC(O)CN>[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([C:15](=[O:18])[CH2:16][NH:2][CH:12]([CH3:7])[CH3:11])[CH:9]=[CH:10][C:11]=2[OH:13])[CH:6]=[CH:5][C:3]1=[O:4]

Participants

3

Reactant 1

HCID 135332255-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one

Product 1

HCID 13533227HCID 13533227, compoundYield 133.2%

Reagents, catalysts & solvents 1

HCID 41-Amino-2-propanolSolvent

Procedure

10 ml of isopropanolamine (III) was added to 1.6 g of 1-methyl-5-chloroacetyl-8-hydroxycarbostyril (IV) prepared as described in Example 2, and the mixture was allowed to react at a temperature of 35° C. for 2 hours while stirring. The reaction mixture was concentrated under reduced pressure, and the residue was distilled azeotropically with ethanol to dryness. The resulting residue was dissolved in 20 ml of ethanol, and the solution was filtered to recover the insoluble material which was then dissolved in hot ethanol. The solution was adjusted to a pH of 2-3 with concentrated hydrochloric acid and cooled with ice. The precipitate formed was filtered and dissolved in 20 ml of water. The solution was adjusted to a pH of 6.5-7.5 with sodium bicarbonate and the precipitate formed was filtered and recrystallized from ethanol to obtain 1.1 g of white amorphous 1-methyl-5-isopropylaminoacetyl-8-hydroxycarbostyril (IIa) having a melting point of 136° to 138° C. (with decomposition).

Workup

  1. customprepared
  2. customto react at a temperature of 35° C. for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. distillationthe residue was distilled azeotropically with ethanol to dryness
  5. dissolutionThe resulting residue was dissolved in 20 ml of ethanol
  6. filtrationthe solution was filtered
  7. customto recover the insoluble material which
  8. dissolutionwas then dissolved in hot ethanol
  9. temperaturecooled with ice
  10. customThe precipitate formed
  11. filtrationwas filtered
  12. dissolutiondissolved in 20 ml of water
  13. customthe precipitate formed
  14. filtrationwas filtered
  15. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a7f452e9efdf4381922e381d42e9ef7d
Source dataset
uspto-grants-1977_05
Patent number
US04022784

Reaction notes

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