Potassium Carbonate → 6-(3-Phthalimidopropoxy)carbostyril

HRID 1856743Notes

Reaction equation

HRID 1856743 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])[CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33]>CN(C)C=O>[C:24]1(=[O:33])[N:23]([CH2:22][CH2:21][CH2:20][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21611N-3-BromopropylphthalimideHCID 1770652,6-Dihydroxyquinoline

Product 1

HCID 117724126-(3-Phthalimidopropoxy)carbostyrilYield 63.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A suspension of 6-hydroxycarbostyril (300 g) and potassium carbonate (308 g) in dimethylformamide (2 liters) is heated with stirring at 70-80° C. for one hour. To the suspension is added N-(3-bromopropyl)phthalimide (498 g), and the mixture is further stirred at the same temperature for 9 hours. The reaction solution is poured into ice-water, and the precipitated crystals are collected by filtration, washed successively with water, ethanol and diethyl ether, and dried to give 6-(3-phthalimidopropoxy)carbostyril (410 g) as a white powder.

Workup

  1. temperatureis heated
  2. stirringthe mixture is further stirred at the same temperature for 9 hours
  3. filtrationthe precipitated crystals are collected by filtration
  4. washwashed successively with water, ethanol and diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-8d24b7e7d1274b21816b89025f4f0af8
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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