4-Toluenesulfonyl chloride → 3,3-Dimethyl-2-(4-(4-methylphenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801290Notes

Reaction equation

HRID 1801290 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[CH3:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:20]([OH:22])=[O:21])[CH:14]=2)[NH:9][CH:8]1[C:5]1[CH:4]=[CH:3][C:2]([NH:1][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:23])=[CH:25][CH:26]=2)(=[O:32])=[O:31])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 674414332-(4-Aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

Product 1

HCID 584761873,3-Dimethyl-2-(4-(4-methylphenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (80 mg, 0.27 mmol) in pyridine (5 mL) was added 4-methylbenzene-1-sulfonyl chloride (57 mg, 0.30 mmol) with ice cooling. Upon completion of the addition, the resultant mixture was allowed to warm back to room temperature and stir overnight. LC-MS showed the reaction was complete. Pyridine was removed in vacuo and the residue was purified by preparative Thin layer chromatography to afford 70 mg of 3,3-dimethyl-2-(4-(4-methylphenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow powder. Yield: 69%; MS (ESI+APCI) M+1=451.20.

Workup

  1. additionUpon completion of the addition
  2. customPyridine was removed in vacuo
  3. customthe residue was purified by preparative Thin layer chromatography

Sources & evidence

ORD record
ord-d716c85f5f4c493b8efd9fa31babb1cd
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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