N-Acetylsulfanilyl chloride → 2-(3-(4-Acetamidophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801263Notes

Reaction equation

HRID 1801263 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=3)[NH:9]2)[CH:5]=[CH:6][CH:7]=1.[C:23]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)(=[O:25])[CH3:24].C(OCC)(=O)C>N1C=CC=CC=1>[C:23]([NH:26][C:27]1[CH:28]=[CH:29][C:30]([S:33]([NH:1][C:2]2[CH:3]=[C:4]([CH:8]3[C:17]([CH3:18])([CH3:19])[CH2:16][C:15]4[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=4)[NH:9]3)[CH:5]=[CH:6][CH:7]=2)(=[O:35])=[O:34])=[CH:31][CH:32]=1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 8857Ethyl AcetateHCID 67441465HCID 67441465, compound

Product 1

HCID 674410122-(3-(4-Acetamidophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 51%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (100 mg, 0.34 mmol) was dissolved in 2 mL of dry pyridine under nitrogen. Then 4-acetamid obenzene-1-sulfonyl chloride (209 mg, 0.85 mmol) was added drop wise to the reaction mixture. The reaction mixture was allowed to stir for 20 h. Thin layer chromatography (petroleum ether:ethyl acetate=1:1, Rf=0.5) showed the reaction was complete. Pyridine was removed in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=1:1) to afford 85 mg of 2-(3-(4-acetamidophenylsulfonamido)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. Yield: 51%. MS (ES+APCI) M+1=494.2.

Workup

  1. customPyridine was removed in vacuo
  2. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-7acae2cc69274211a40ce30223ad0031
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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