Hydrochloric Acid → 1-methyl-6-{3-[(pyridin-3-ylmethyl)amino]propoxy}-1H-quinolin-2-one

HRID 69025Notes

Reaction equation

HRID 69025 reaction equation
Cl.C(O)C.[CH3:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][N:20]([CH2:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)C(=O)C3C=CC=CC=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]1=[O:36]>O>[CH3:5][N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][CH2:19][NH:20][CH2:29][C:30]3[CH:31]=[N:32][CH:33]=[CH:34][CH:35]=3)=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]1=[O:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 86762694N-[3-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-3-ylmethyl)benzamide

Product 1

HCID 867626931-methyl-6-{3-[(pyridin-3-ylmethyl)amino]propoxy}-1H-quinolin-2-oneYield 88.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3N-Hydrochloric acid (5 ml) was added to a ethanol solution (5 ml) of N-[3-(1-Methyl-2-oxo-1,2-dihydroquinolin-6-yloxy)propyl]-N-(pyridin-3-ylmethyl)benzamide (250.1 mg), and stirred for 60 hours while heated under reflux. The reaction mixture was cooled to room temperature. Water was added thereto, washed with ethyl acetate. A saturated sodium hydrogencarbonate aqueous solution was added to the aqueous layer, followed by extraction using dichloromethane. The organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure to give the title compound (168 mg) as a colorless oil.

Workup

  1. temperaturewhile heated
  2. temperatureunder reflux
  3. washwashed with ethyl acetate
  4. additionA saturated sodium hydrogencarbonate aqueous solution was added to the aqueous layer
  5. extractionfollowed by extraction
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate, and condensed under reduced pressure

Sources & evidence

ORD record
ord-bfa5b6e8eb354dc29f5b9f57e1488b46
Source dataset
uspto-grants-2014_09
Patent number
US08822453B2

Reaction notes

Loading…