Chlorosuccinimide → 6-Bromo-5-chloropyridin-2-amine

HRID 1521959Notes

Reaction equation

HRID 1521959 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[Cl:9]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[Cl:9]

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 3008092-Amino-6-bromopyridine

Product 1

HCID 534011936-Bromo-5-chloropyridin-2-amine

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-bromopyridin-2-amine (10 g, 58 mmol) in acetonitrile (150 mL) was added 1-chloropyrrolidine-2,5-dione (8.1 g, 60 mmol) and the mixture was heated at 80° C. for 10 hours. The mixture was diluted with ethyl acetate (200 mL) and washed with water. The organic phase was concentrated and purified by column chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound. LCMS: 208 (M+H)+.

Workup

  1. washwashed with water
  2. concentrationThe organic phase was concentrated
  3. custompurified by column chromatography (silica gel, 30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-96a9d554444142d3b6f9b07200c100d2
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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