Sulfuric Acid → 6-Chloro-3-nitropicolinamide

HRID 50768Notes

Reaction equation

HRID 50768 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1.[OH:13]S(O)(=O)=O>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:13])[C:5]([N+:10]([O-:12])=[O:11])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 133817056-Chloro-3-nitropyridine-2-carbonitrile

Product 1

HCID 105360876-Chloro-3-nitropicolinamideYield 73%

Procedure

A solution of 6-chloro-3-nitropicolinonitrile (1.00 g, 5.45 mmol) in 90% H2SO4 (15 mL) is warmed at 70° C. for 3.5 h, and then poured into ice-water. The mixture is extracted four times with EtOAc and the combined extracts worked up to give 6-chloro-3-nitropicolinamide (0.80 g, 73%). 1H NMR (DMSO) δ 8.55 (1H, d, J=8.5 Hz), 8.31, 8.04 (1H, 1H, 2 brs), 7.93 (1H, d, J=8.5 Hz).

Workup

  1. extractionThe mixture is extracted four times with EtOAc

Sources & evidence

ORD record
ord-45fee95ef8cf41609db0d7e6dfa7edd0
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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