Potassium Hydroxide → HCID 9799122, compound

HRID 377621Notes

Reaction equation

HRID 377621 reaction equation
[CH:1]([N:4]([CH:30]([CH3:32])[CH3:31])[CH2:5][CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:10](=[O:24])[C:9]=1C(OCC)=O)([CH3:3])[CH3:2].[OH-].[K+]>CS(C)=O.O>[CH:30]([N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6][NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:10](=[O:24])[CH:9]=1)([CH3:31])[CH3:32]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19356229HCID 19356229, compound

Product 1

HCID 9799122HCID 9799122, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Dissolved in 50 ml of dimethylsulfoxide were 1.31 g (3 mmol) of ethyl 4-(2-diisopropylaminoethylamino)-2-oxo-1-phenyl-1,2-dihydroquinoline-3-carboxylate (Compound No. 7), followed by the addition of a solution of 0.68 g (10 mmol) of potassium hydroxide in 6 ml of water. They were reacted at 60° C. for 4 hours. The reaction mixture was poured into ice water, and the resulting precipitate was collected by filtration, washed with water and then dried. The resulting powder was dissolved in chloroform, purified by chromatography on a silica gel column, and then recrystallized from isopropyl ether, whereby 0.78 g of 4-(2-diisopropylaminoethylamino)-1-phenyl-1,2-dihydroquinolin-2-one (Compound No. 43) was obtained (yield: 71.6%).

Workup

  1. customThey were reacted at 60° C. for 4 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried
  5. dissolutionThe resulting powder was dissolved in chloroform
  6. custompurified by chromatography on a silica gel column
  7. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-1f1e032e779e44e0a83d4c3e882c8371
Source dataset
uspto-grants-2000_02
Patent number
US06028081

Reaction notes

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