8-Aminoquinoline → 4-Chloroquinolin-8-amine

HRID 1663306Notes

Reaction equation

HRID 1663306 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.[Cl:12]N1C(=O)CCC1=O>CC(O)C>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[Cl:12]

Participants

4

Reactant 2

HCID 113598-AminoquinolineHCID 31398Chlorosuccinimide

Product 1

HCID 126042744-Chloroquinolin-8-amineYield 34%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

8-amino quinoline (4.5 g, 31.3 mmol), N-chlorosuccinimide (4.80 g, 36 mmol) was taken up in iPrOH (50 mL) at 60° C. The mixture was heated to reflux and stirred for 20 min. The solution was cooled to 25° C. and concentrated to ⅓ original volume. The mixture was partitioned between CH2Cl2 and water. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash chromatography (5:1 hexanes/EtOAc) to afford 1.90 g (34%) of a 8-amino-4-chloro-quinoline product.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customThe mixture was partitioned between CH2Cl2 and water
  5. extractionThe aqueous layer was extracted with CH2Cl2
  6. dry with materialThe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash chromatography (5:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-b7a6a4e82fbe4705bdfc9e68ad8bd688
Source dataset
uspto-grants-2011_10
Patent number
US08034933B2

Reaction notes

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