Hydrochloric Acid → (8-Amino-5-chloro-quinolin-7-yl)-(4-fluoro-phenyl)-methanone

HRID 513681Notes

Reaction equation

HRID 513681 reaction equation
[Cl:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:21])=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2.Cl>C(Cl)(Cl)(Cl)Cl>[NH2:9][C:10]1[C:11]([C:20]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)=[O:21])=[CH:12][C:13]([Cl:1])=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31398ChlorosuccinimideHCID 68183219(8-Amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone

Product 1

HCID 68183190(8-Amino-5-chloro-quinolin-7-yl)-(4-fluoro-phenyl)-methanoneYield 43%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
80 °C

Procedure

N-Chlorosuccinimide (0.12 g, 0.93 mmol) was added to a solution of (8-amino-quinolin-7-yl)-(4-fluoro-phenyl)-methanone 367 (0.25 g, 0.93 mmol) in CCl4 (3 ml) followed by HCl (cat) and the mixture was heated at 80° C. for 4 h. After cooling, the mixture was quenched with water and the aqueous phase was extracted with EtOAc. The organic phase was washed with 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 (0.1 g, 43%).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was quenched with water
  3. extractionthe aqueous phase was extracted with EtOAc
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by column chromatography with DCM as the eluent

Sources & evidence

ORD record
ord-cf2719c33c2649cea98532a175f47e80
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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