Hydrochloric Acid → HCID 58494797, compound
Reaction equation
[Cl:1][C:2]1[C:3]2[CH2:17][CH2:16][N:15](C(OCC)=O)[CH2:14][CH2:13][C:4]=2[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[OH-].[K+].Cl.[OH-].[Na+]>C(O)CO>[Cl:1][C:2]1[C:3]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13][C:4]=2[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
To 1.865 g of ethyl 11-chloro-2-oxo-1,2,3,4,6,7,9,10-octahydro-8H-azepino[4,5-g]quinoline-8-carboxylate were added 20 mL of ethylene glycol and 20 mL of a 40% aqueous potassium hydroxide solution, followed by heating to 120° C. for 18 hours. The reaction mixture was ice-cooled and adjusted to pH 1 by the addition of concentrated hydrochloric acid, followed by stirring for 1 hour. The reaction mixture was alkalified by the addition of a 1 M aqueous sodium hydroxide solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure to obtain 1.451 g of 11-chloro-1,3,4,6,7,8,9,10-octahydro-2H-azepino[4,5-g]quinolin-2-one as a brown solid. To 60 mg of 11-chloro-1,3,4,6,7,8,9,10-octahydro-2H-azepino[4,5-g]quinolin-2-one were added 1 ml of EtOAc and then EtOH, followed by dissolution under heating. The precipitated solid was collected by filtration to obtain 29.5 mg of 11-chloro-1,3,4,6,7,8,9,10-octahydro-2H-azepino[4,5-g]quinolin-2-one as a white solid.
Workup
- temperaturecooled
- extractionfollowed by extraction with chloroform
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-18cbfdcb6297421e8fe6deacf7f00dac
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09108977B2
Reaction notes
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