Isopropylamine → HCID 21436084, compound

HRID 2397583Notes

Reaction equation

HRID 2397583 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][CH3:14])[CH:6]=[CH:5][C:3]1=[O:4].[CH:19]([NH2:22])([CH3:21])[CH3:20]>C(O)(C)C>[CH3:1][N:2]1[C:12]2[C:7](=[C:8]([C:15](=[O:18])[CH2:16][NH:22][CH:19]([CH3:21])[CH3:20])[CH:9]=[CH:10][C:11]=2[O:13][CH3:14])[CH:6]=[CH:5][C:3]1=[O:4]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 135332255-(Chloroacetyl)-8-methoxy-1-methylquinolin-2(1H)-one

Product 1

HCID 21436084HCID 21436084, compoundYield 13.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2.7 g of 1-methyl-5-chloroacetyl-8-methoxycarbostyril (IV) prepared as described in Example 1 was dissolved in 40 ml of isopropanol, and 9 g of isopropylamine (III) was added to the solution while heating the solution at a temperature of 55° to 60° C. over a period of 1.5 hours. After completion of the addition, the mixture was allowed to react for one hour while stirring. The reaction mixture was concentrated under reduced pressure and the resulting residue was dissolved in 40 ml of isopropanol. The solution was then filtered to remove any insoluble material, and the filtrate was adjusted to a pH of 2-3 with concentrated hydrochloric acid. The mixture was cooled with ice and the precipitate formed was filtered and recrystallized from ethanol to obtain 0.4 g of white amorphous 1-methyl-5-isopropylaminoacetyl-8-methoxycarbostyril (IIb) hydrochloride. The product thus obtained was confirmed by elemental analysis and IR spectral analysis.

Workup

  1. temperaturewhile heating the solution at a temperature of 55° to 60° C. over a period of 1.5 hours
  2. additionAfter completion of the addition
  3. customto react for one hour
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in 40 ml of isopropanol
  6. filtrationThe solution was then filtered
  7. customto remove any insoluble material
  8. temperatureThe mixture was cooled with ice
  9. customthe precipitate formed
  10. filtrationwas filtered
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-04208a1b4c154eafb4465087fbd6a075
Source dataset
uspto-grants-1977_05
Patent number
US04022784

Reaction notes

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