Chlorosuccinimide → 2-Amino-4,5-dichloro-3-nitropyridine

HRID 63587

Reaction equation

HRID 63587 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[C:7]([Cl:12])=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[N+:9]([O-:11])=[O:10]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 40716944-Chloro-3-nitropyridin-2-amine

Product 1

HCID 468676602-Amino-4,5-dichloro-3-nitropyridineYield 103.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Chloro-3-nitropyridin-2-amine (0.10 g, 0.58 mmol) was dissolved in dry acetonitrile (20 mL). To the stirred solution was then added N-chlorosuccinimide (0.094 g, 0.70 mmol), and the reaction mixture was heated at 80° C. for 1 h. Volatiles were removed in vacuo and the residue purified by silica column chromatography (elution with dichloromethane) to provide the title compound as a pale brown powder (0.125 g, 85%). 1H-NMR (500 MHz, DMSO-d6) 7.35 (s, 2H, NH2), 8.36 (s, 1H, 6-H).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue purified by silica column chromatography (elution with dichloromethane)

Sources & evidence

ORD record
ord-5cbf9c16164641f987fd0eb820ed7ad2
Source dataset
uspto-grants-2016_09
Patent number
US09447092B2

Linked notes

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