N-bromobutanimide → 5-Bromo-6-chloropyridin-2-amine

HRID 1625997Notes

Reaction equation

HRID 1625997 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Br:9]N1C(=O)CCC1=O>C(#N)C>[Br:9][C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2062462-Amino-6-chloropyridine

Product 1

HCID 223492035-Bromo-6-chloropyridin-2-amineYield 86.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Chloropyridin-2-amine (2.0 g) was dissolved in acetonitrile (40 ml). N-Bromosuccinimide (3.1 g) was added and the mixture was stirred under shading at room temperature for 13 hours. The reaction solution was concentrated and the resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (2.8 g).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe resulting residue was purified by silica gel column chromatography (developed with ethyl acetate-hexane)

Sources & evidence

ORD record
ord-a892c2fdd07b48b6b444fa5ce32e57e0
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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