Sodium Bicarbonate → 1-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

HRID 1891385Notes

Reaction equation

HRID 1891385 reaction equation
[CH3:1][C:2]1([CH3:12])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4][CH2:3]1.C([O-])(O)=O.[Na+].[Br:18][C:19]1[C:20]([Cl:30])=[CH:21][C:22]([F:29])=[C:23]([S:25](Cl)(=[O:27])=[O:26])[CH:24]=1>O.C(#N)C>[Br:18][C:19]1[C:20]([Cl:30])=[CH:21][C:22]([F:29])=[C:23]([S:25]([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([CH3:12])([CH3:1])[CH2:3][CH2:4]2)(=[O:27])=[O:26])[CH:24]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinolineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

Product 1

HCID 684692731-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinolineYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

To 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (2.2 g, 13.66 mmol) in a mixture of water (60 mL) and acetonitrile (40 mL) containing NaHCO3 (3.44 g, 41.0 mmol), was added 5-bromo-4-chloro-2-fluoro-benzenesulfonyl chloride (4.2 g, 13.66 mmol) in acetonitrile (20 mL) slowly with vigorous stirring. After addition, the mixture was stirred for 3 hrs. The resulting precipitate was filtered, washed with hexane and dried to yield 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline as a light brown solid (5.0 g).

Workup

  1. additionAfter addition
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with hexane
  4. customdried

Sources & evidence

ORD record
ord-d6c6b2193f91457c8d5db69f123b7a98
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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