Ammonia → 6-Chloro-3-nitropyridin-2-ylamine

HRID 555222Notes

Reaction equation

HRID 555222 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[NH3:12]>CO>[NH2:12][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 27240356-Chloro-3-nitropyridin-2-ylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-Dichloro-3-nitropyridine was suspended in MeOH, and the mixture was treated with ammonia at room temperature for 12 hours to yield 2-amino-3-nitro-6-chloropyridine. This was then treated with an ethanolic:aqueous solution of sodium hydroxide (10 M) at reflux to give 2-amino-3-nitro-6-(1H)-pyridinone. This was then treated with N-iodosuccinimide (1.05 equivalents) in dimethylformamide at room temperature to yield 2-amino-3-nitro-5-iodo-6-(1H)-pyridinone.

Sources & evidence

ORD record
ord-c84788065bf1426293d0662106e060cb
Source dataset
uspto-grants-2011_11
Patent number
US08053212B1

Reaction notes

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