Sodium Chloride → N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide

HRID 1154949Notes

Reaction equation

HRID 1154949 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[OH-].[K+].[I-].[Na+].[CH3:17][N:18]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:19](=[O:24])[CH2:20][CH2:21][CH2:22]Cl.[Na+].[Cl-]>CS(C)=O>[CH3:17][N:18]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[C:19]([CH2:20][CH2:21][CH2:22][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2)=[O:24]

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 132082974-Chloro-N-cyclohexyl-N-methylbutanamide

Product 1

HCID 13200334N-Cyclohexyl-N-methyl-4-((2-oxo-1,2,3,4-tetrahydroquinolin-6-yl)oxy)butanamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3.2 Grams of 6-hydroxy-3,4-dihydrocarbostyril, 0.9 g of potassium hydroxide, 3.2 g of sodium iodide and 5.0 g of N-methyl-N-(4-chlorobutyryl)cyclohexylamine are added to 50 ml of dimethylsulfoxide, and the mixture is agitated at 70° to 80° C. for 4.5 hours. After the reaction, the reaction solution is poured into 400 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The thus obtained crude crystals are then recrystallized from benzene-petroluem ether to obtain 2.9 g of 6-[3-(N-methyl-N-cyclohexylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needlelike crystals with melting point of 144°-146° C.

Workup

  1. customAfter the reaction
  2. filtrationthe precipitated crystals are filtered out
  3. washwashed with water
  4. customThe thus obtained crude crystals
  5. customare then recrystallized from benzene-petroluem ether

Sources & evidence

ORD record
ord-e0e2ce78aed047a99e5743eeac424e52
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

Loading…