Dimethylformamide → 5-Bromo-3-chloropyridin-2-amine

HRID 81634Notes

Reaction equation

HRID 81634 reaction equation
[Cl:1]N1C(=O)CCC1=O.CN(C)C=O.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[N:19][CH:20]=1.[OH-].[Na+]>O>[Br:14][C:15]1[CH:16]=[C:17]([Cl:1])[C:18]([NH2:21])=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 31398ChlorosuccinimideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 123706695-Bromo-3-chloropyridin-2-amineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, 1-chloropyrrolidine-2,5-dione (10 g, 76 mmol) was added to an N,N-dimethylformamide solution (30 ml) of 5-bromopyridine-2-amine (12 g, 69 mmol), and stirred for 4 hours. The reaction solution was diluted with water, neutralized with aqueous 5 N sodium hydroxide solution, and extracted with diethyl ether. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=25:25:50) to obtain 5-bromo-3-chloropyridine-2-amine (12.6 g, yield: 88%) as a brown solid.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with saturated saline water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=25:25:50)

Sources & evidence

ORD record
ord-2a84e80d2a77478db45348c51e33ab6d
Source dataset
uspto-grants-2014_09
Patent number
US08846700B2

Reaction notes

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