8-Aminoquinoline → HCID 22670868, compound

HRID 1006388Notes

Reaction equation

HRID 1006388 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH2:12]([S:16](Cl)(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15]>N1C=CC=CC=1>[CH2:12]([S:16]([NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2)(=[O:18])=[O:17])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 754301-Butanesulfonyl chloride

Product 1

HCID 22670868HCID 22670868, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The reaction of 5.0 g (0.0347 mole) of 8-aminoquinoline with 5.43 g (0.0347 mole) of n-butanesulfonyl chloride was carried out in 10 ml of pyridine at room temperature. After 2 hours from the start of the reaction, the reaction mixture was washed with water, extracted with diethyl ether, purified by column chromatography and concentrated to give 10.32 g (0.032 mole, 92%) of 8-(n-butylsulfonamido)quinoline. Then, 5.0 g (0.019 mole) of the 8-(n-butylsulfonamido)quinoline, 2.12 g (0.019 mole ) of zinc chloride and 4.76 g (0.047 mole) of triethylamine were suspended in 30 ml of ethanol and allowed to react at room temperature. After 3 hours, the separated yellow powder was filtered, washed with ethanol and purified by column chromatography to give 8.62 g (91.0%) of Compound N as yellow crystals. The maximum PL wavelength of this compound in chloroform was 510 nm.

Workup

  1. customAfter 2 hours from the start of the reaction
  2. washthe reaction mixture was washed with water
  3. extractionextracted with diethyl ether
  4. custompurified by column chromatography
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-88aadb1f85374169b99be28162160027
Source dataset
uspto-grants-2004_09
Patent number
US06790540B2

Reaction notes

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