Chlorosuccinimide → 4-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acid

HRID 494697Notes

Reaction equation

HRID 494697 reaction equation
[Cl:1]N1C(=O)CCC1=O.Cl.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]([Cl:27])[CH:19]=2)=[C:13]([Cl:28])[CH:12]=1>CN(C=O)C.S(=O)(O)[O-].[Na+].O>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:23]([C:24]([OH:26])=[O:25])=[CH:22][N:21]=[C:20]([Cl:27])[C:19]=2[Cl:1])=[C:13]([Cl:28])[CH:12]=1

Participants

6

Reactant 2

HCID 31398ChlorosuccinimideHCID 865967774-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid hydrochloride salt

Product 1

HCID 116612174-(4-Bromo-2-chlorophenylamino)-5,6-dichloronicotinic acidYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 23665763Sodium BisulfiteSolvent

Procedure

N-Chlorosuccinimide was (13.0 g, 99.0 mmol) added to a suspension of 4-(4-bromo-2-chlorophenylamino)-6-chloronicotinic acid (24) (32.54 g, 89.9 mmol) in DMF (500 mL). The suspension was allowed to stir at room temperature overnight. The reaction mixture was diluted with saturated sodium bisulfite (200 mL) and water (1L) resulting in formation of a thick white precipitate which was isolated by filtration and washed with water. The solids were dissolved into THF. Two volumes of diethyl ether were added and the organic solution washed with brine, dried over NaSO4, filtered, and concentrated in vacuo to provide an orange solid. The solid was triturated with diethyl ether to provide the desired product as an off-white solid (25) (13.34 g, 37%). MS (APCI−) m/z 393, 395, 397 (M-; Cl, Br pattern) detected.

Workup

  1. customresulting in formation of a thick white precipitate which
  2. customwas isolated by filtration
  3. washwashed with water
  4. dissolutionThe solids were dissolved into THF
  5. additionTwo volumes of diethyl ether were added
  6. washthe organic solution washed with brine
  7. dry with materialdried over NaSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide an orange solid
  11. customThe solid was triturated with diethyl ether

Sources & evidence

ORD record
ord-b1db52fe612e4d469da05633f09f2af7
Source dataset
uspto-grants-2009_05
Patent number
US07538120B2

Reaction notes

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