Sodium Chloride → 2-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester

HRID 2382710Notes

Reaction equation

HRID 2382710 reaction equation
[CH3:1][O:2][C:3](=[O:32])[CH:4]([C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Br:16])=[CH:11][C:10]=1[S:17]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH3:31])([CH3:30])[CH2:22][CH2:21]1)(=[O:19])=[O:18])C(OC)=O.[Na+].[Cl-]>CS(C)=O.O>[CH3:1][O:2][C:3](=[O:32])[CH2:4][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Br:16])=[CH:11][C:10]=1[S:17]([N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([CH3:30])([CH3:31])[CH2:22][CH2:21]1)(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 5234Sodium ChlorideHCID 684691712-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-malonic acid dimethyl ester

Product 1

HCID 684691412-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl esterYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

2-[4-Bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-malonic acid dimethyl ester (0.72 g, 1.32 mmol) was heated at 120° C. for 5 hrs in DMSO which contained NaCl (153.5 mg, 2.65 mmol) and 2 drops of water. After cooling to rt, the mixture was extracted with ethyl acetate, washed with water and brine, and was dried over MgSO4. Filtration and concentration yielded a residue which was purified via silica gel flash column chromatography eluting with hexane/ethyl acetate (100/15) to give 2-[4-bromo-5-chloro-2-(4,4-dimethyl-3,4-dihydro-2H-quinoline-1-sulfonyl)-phenyl]-acetic acid methyl ester (512 mg). MS: 487.9 (M+H)+; tR=2.75 min (method 1)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with water and brine
  3. dry with materialwas dried over MgSO4
  4. filtrationFiltration and concentration
  5. customyielded a residue which
  6. customwas purified via silica gel flash column chromatography
  7. washeluting with hexane/ethyl acetate (100/15)

Sources & evidence

ORD record
ord-23faa14a0d3840518fae72c673cd94a2
Source dataset
uspto-grants-2012_09
Patent number
US08263588B2

Reaction notes

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