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

HRID 2252086Notes

Reaction equation

HRID 2252086 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

N-(2-Dimethylamino-ethyl)-3-nitro-benzenesulfonamide (3). To a solution of 3-nitrobenzenesulfonyl chloride (1, 1.0 g, 4.51 mmol) in anhydrous CH2Cl2 (9.0 mL) was added N,N-dimethyl-ethylenediamine (2, 0.5 mL, 4.55 mmol) dropwise. The resulting solution was stirred at room temperature overnight before it was diluted with EtOAc (80 mL). The organic mixture was washed with saturated NaHCO3 (90 mL), brine (90 mL), and dried over MgSO4. The solids were filtered and the filtrate was concentrated on a rotavap to give 3 as a foam (0.8 g) which was used in the next step without further purification. Step 2. 3-Amino-N-(2-dimethylamino-ethyl)-benzenesulfonamide (4). A solution of 3 (0.8 g) in ethanol (10 mL) was subjected to catalytic hydrogenation (10% Pd/C, Degussa, 0.8 g, 3 drops of AcOH, 1 atm.) overnight. To work up, the solids were filtered the filtrate was dried under vacuum to afford 4 as a solid (0.71 g) which was used in the next step without further purification. Step 3. N-(2-Dimethylamino-ethyl)-3-(2-methyl-quinolin-4-ylamino)-benzenesulfonamide. 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. customwas used in the next step without further purification
  2. customwas subjected to catalytic hydrogenation (10% Pd/C, Degussa, 0.8 g, 3 drops of AcOH, 1 atm.) overnight
  3. filtrationthe solids were filtered the filtrate
  4. customwas dried under vacuum
  5. customto afford 4 as a solid (0.71 g) which
  6. customwas used in the next step without further purification
  7. temperatureThe resulting mixture was heated
  8. customwas removed under reduced pressure
  9. extractionthe basic solution was extracted with EtOAc (2×20 mL)
  10. dry with materialThe combined organic layers were dried over MgSO4
  11. filtrationthe solids were filtered
  12. concentrationthe filtrate was concentrated on a rotavap
  13. customThe residue was purified on Florisil®

Sources & evidence

ORD record
ord-c33087a5bbd14802bb3dcb61e3918a7d
Source dataset
uspto-grants-2008_01
Patent number
US07320989B2

Reaction notes

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