Sulfuric Acid → 2,5,6-Trichloropyridine-3-carboxamide

HRID 2284489Notes

Reaction equation

HRID 2284489 reaction equation
[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:3]=1[C:4]#[N:5].S(=O)(=O)(O)[OH:13]>>[Cl:1][C:2]1[N:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:3]=1[C:4]([NH2:5])=[O:13]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 229063392,5,6-Trichloropyridine-3-carbonitrile

Product 1

HCID 537509302,5,6-Trichloropyridine-3-carboxamide

Procedure

A solution of 2,5,6-trichloronicotinonitrile (30 g, 144.92 mmol, 1.00 equiv) in sulfuric acid (98%, 162 mL, 1.00 equiv) was stirred for 1 h at 60° C. in an oil bath. The reaction mixture was cooled and then quenched by the addition of water/ice. The solid was collected by filtration and dried in an oven under reduced pressure. This resulted in 26 g of 2,5,6-trichloronicotinamide as a white solid. LC-MS (ES, m/z): 225 [M+H]+. 1H-NMR (300 MHz, DMSO-d6) δ (ppm) 9.38 (1H, s), 8.12 (1H, s), 7.95 (1H, s).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customquenched by the addition of water/ice
  3. filtrationThe solid was collected by filtration
  4. customdried in an oven under reduced pressure
  5. customThis resulted in 26 g of 2,5,6-trichloronicotinamide as a white solid

Sources & evidence

ORD record
ord-3cadeedc22e849a2a54ea618052d34e8
Source dataset
uspto-grants-2015_09
Patent number
US09145429B2

Reaction notes

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