Aniline → HCID 68183029, compound

HRID 513639Notes

Reaction equation

HRID 513639 reaction equation
Cl[S:2]([OH:5])(=O)=[O:3].[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][CH:13]=[CH:12]2.P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:24]1([NH:23][S:2]([NH:6][C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:16]=2[N:15]=[CH:14][CH:13]=[CH:12]3)(=[O:5])=[O:3])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 6115AnilineHCID 113598-AminoquinolineHCID 24638Chlorosulfonic acidHCID 24819Phosphorus pentachlorideHCID 81531Diisopropylethylamine

Product 1

HCID 68183029HCID 68183029, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonic acid (260 mg, 2.2 mmol) in DCM was added to a solution of 8-aminoquinoline (300 mg, 2.08 mmol) and TEA (310 mg, 3.12 mmol) in dry DCM (10 ml) at 0° C. and the mixture was stirred for 30 min. The reaction was allowed to warm to room temperature and stirring was continued for 1 h. PCl5 (460 mg, 2.20 mmol) was added to the reaction and the mixture was heated under reflux for 1 h, then allowed to cool to room temperature. Aniline (770 mg, 8.3 mmol) and DIPEA (0.72 ml, 4.16 mmol) were added and the reaction stirred at room temperature for 2.5 h. The reaction was quenched with water and extracted with DCM. The organic phase was washed with water, brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by column chromatography with DCM as the eluent to give the title compound (70 mg, 11%).

Workup

  1. stirringstirring
  2. waitwas continued for 1 h
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 h
  5. temperatureto cool to room temperature
  6. stirringthe reaction stirred at room temperature for 2.5 h
  7. customThe reaction was quenched with water
  8. extractionextracted with DCM
  9. washThe organic phase was washed with water, brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated in vacuo
  12. customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record
ord-9d5c66e053e84933b724be49750e5a04
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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