Hydrochloric Acid → 6-(3-Aminopropoxy)carbostyril

HRID 1856744Notes

Reaction equation

HRID 1856744 reaction equation
C1(=O)[N:5]([CH2:6][CH2:7][CH2:8][O:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]3)C(=O)C2=CC=CC=C12.O.NN.Cl>C(O)C>[NH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 117724126-(3-Phthalimidopropoxy)carbostyril

Product 1

HCID 100136326-(3-Aminopropoxy)carbostyrilYield 74.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 6-(3-phthalimidopropoxy)carbostyril (300 g) in ethanol (3 liters) is added hydrazine monohydrate (46 g), and the mixture is refluxed for 8 hours. After the mixture is allowed to cool, the precipitated crystals are collected by filtration, suspended in water, and the suspension thus obtained is acidified with conc. hydrochloric acid, and stirred for one hour. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure to remove the solvent. The residue is neutralized to pH 7 with a 15% aqueous sodium hydroxide solution. The precipitated crystals are collected by filtration, and washed successively with ethanol and diethyl ether, and dried to give 6-(3-aminopropoxy)carbostyril (140 g) as a white powder.

Workup

  1. temperaturethe mixture is refluxed for 8 hours
  2. temperatureto cool
  3. filtrationthe precipitated crystals are collected by filtration
  4. customthe suspension thus obtained
  5. customThe insoluble materials are removed by filtration
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customto remove the solvent
  8. filtrationThe precipitated crystals are collected by filtration
  9. washwashed successively with ethanol and diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-e6fddc6f72094a0381cd978cdd7b4772
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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