Potassium Carbonate → 6-(3-Phenoxycarbonylaminopropoxy)carbostyril

HRID 1856766Notes

Reaction equation

HRID 1856766 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.C(=O)([O-])[O-].[K+].[K+].[C:24](Cl)(=[O:32])[O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O.C(#N)C>[O:25]([C:24]([NH:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 114141486-(3-aminopropoxy)-1H-quinolin-2-one;hydrochloride

Product 1

HCID 221326106-(3-Phenoxycarbonylaminopropoxy)carbostyrilYield 90.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a mixture of water (50 ml) and acetonitrile (50 ml) are added 6-(3-aminopropoxy)carbostyril hydrochloride (5.0 g) and potassium carbonate (3.4 g) at room temperature. The mixture is stirred at room temperature for 2 hours, and cooled to -5° C. To the mixture is added dropwise phenyl chlorocarbonate (3.9 g) while the temperature of the mixture is kept below 0° C. The mixture is stirred at the same temperature for 1 hour, and thereto is added water (100 ml), and then the mixture is further stirred for 0.5 hour. The precipitated crystals are collected by filtration, and washed successively with water and acetone to give 6-(3-phenoxycarbonylaminopropoxy)carbostyril (6.0 g) as a white powder.

Workup

  1. temperaturecooled to -5° C
  2. customis kept below 0° C
  3. stirringThe mixture is stirred at the same temperature for 1 hour
  4. stirringthe mixture is further stirred for 0.5 hour
  5. filtrationThe precipitated crystals are collected by filtration
  6. washwashed successively with water and acetone

Sources & evidence

ORD record
ord-42764983a41c4be598441f4d5877af9a
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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