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

HRID 1801324Notes

Reaction equation

HRID 1801324 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:22]([CH3:24])([CH3:23])[CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=3)[NH:14]2)[CH:10]=[CH:11][CH:12]=1>N1C=CC=CC=1>[CH3:23][C:22]1([CH3:24])[CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([C:25]([OH:27])=[O:26])[CH:19]=2)[NH:14][CH:13]1[C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])[CH:8]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67441465HCID 67441465, compound

Product 1

HCID 674418473,3-Dimethyl-2-(3-(methylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acidYield 21.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a round-bottomed flask, methanesulfonyl chloride (0.07 mL, 0.84 mmol) was added dropwise to a solution of 2-(3-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (0.1 g, 0.34 mmol) in dry pyridine (2 mL) was allowed to stir at room temperature for 1 h. The pyridine was removed under vacuum. The residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=1:1) to afford 3,3-dimethyl-2-(3-(methylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a white solid (27 mg, yield: 21.3%); MS (ES+APCI) M+1=375.1.

Workup

  1. customThe pyridine was removed under vacuum
  2. customThe residue was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-533cc42990d846948fa418568697c295
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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