4-Chloro-2-methylquinoline → HCID 58958077, compound

HRID 914961Notes

Reaction equation

HRID 914961 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:8]([NH:11][CH2:12][CH2:13][N:14]([CH3:16])[CH3:15])(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([CH3:28])[CH:19]=1>C(O)C.Cl>[CH3:15][N:14]([CH3:16])[CH2:13][CH2:12][NH:11][S:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([CH3:28])[CH:19]=2)[CH:3]=1)(=[O:10])=[O:9]

Participants

5

Reactant 2

HCID 779734-Chloro-2-methylquinolineHCID 167906463-amino-N-[2-(dimethylamino)ethyl]benzenesulfonamide

Product 1

HCID 58958077HCID 58958077, compoundYield 3.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of 4 (0.3 g, 1.23 mmol) and 4-chloroquinaldine (5, 0.26 mL, 1.29 mmol) in ethanol (10 mL) were added 2 drops of conc. HCl. The resulting mixture was heated under reflux overnight before ethanol was removed under reduced pressure. The residue was basified with saturated NaHCO3 (aq. 20 mL) and the basic solution was extracted with EtOAc (2×20 mL). The combined organic layers were dried over MgSO4, the solids were filtered and the filtrate was concentrated on a rotavap. The residue was purified on Florisil® to give the title compound as an orange solid (15 mg).

Workup

  1. temperatureThe resulting mixture was heated
  2. customwas removed under reduced pressure
  3. extractionthe basic solution was extracted with EtOAc (2×20 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationthe solids were filtered
  6. concentrationthe filtrate was concentrated on a rotavap
  7. customThe residue was purified on Florisil®

Sources & evidence

ORD record
ord-7b7f009326a84989ad49f2c694a537be
Source dataset
uspto-grants-2007_09
Patent number
US07265122B2

Reaction notes

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