Pyridine → N-3-Quinolinylbenzenesulfonamide

HRID 394554Notes

Reaction equation

HRID 394554 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(OCC)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:1][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH:3]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 113753-Aminoquinoline

Product 1

HCID 16654646N-3-Quinolinylbenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-aminoquinoline (7.2 g, 50 mmol) in acetonitrile (150 mL) was added pyridine (25 mL) and the resulting mixture was cooled to 0° C. A solution of benzenesulfonyl chloride (7 mL, 55 mmol) in acetonitrile (20 mL) was added dropwise over 30 minutes. The mixture was allowed to warm to rt and stirred for 18 hours. The mixture was diluted with ethyl acetate (100 mL) and washed successively with 1N HCl, brine and saturated CuSO4, dried (MgSO4), and concentrated in vacuo to afford an oil. Purification by flash silica gel column chromatography eluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid. MS; (M+H)+=285

Workup

  1. temperatureto warm to rt
  2. washwashed successively with 1N HCl, brine and saturated CuSO4
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customPurification by flash silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid

Sources & evidence

ORD record
ord-be7dfc7e9e8c4e32b0ec01ae27d2bc73
Source dataset
uspto-grants-2003_08
Patent number
US06602883B1

Reaction notes

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