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

HRID 1891387Notes

Reaction equation

HRID 1891387 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-abd6f065437742f38ebc30c091e1a4e0
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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