Ethyl Acetate → 3,3-Dimethyl-2-(3-(1-methylethylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

HRID 1801258Notes

Reaction equation

HRID 1801258 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.[CH3:23][CH:24]([S:26](Cl)(=[O:28])=[O:27])[CH3:25].C(OCC)(=O)C>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:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:26]([CH:24]([CH3:25])[CH3:23])(=[O:28])=[O:27])[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 824082-Propanesulfonyl chlorideHCID 67441465HCID 67441465, compound

Product 1

HCID 674414833,3-Dimethyl-2-(3-(1-methylethylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 36.8%

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 propane-2-sulfonyl chloride (0.1 mL, 0.89 mmol) was added drop wise to the reaction mixture. The reaction mixture was allowed to stir overnight. 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 50 mg of 3,3-dimethyl-2-(3-(1-methylethylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. Yield: 36.8%. MS (ES+APCI) M+1=403.1.

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-ff198867c0f04db39193c638ea840edd
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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