Sulfuric Acid → 3-Nitro-5-(trifluoromethyl)picolinamide

HRID 627719Notes

Reaction equation

HRID 627719 reaction equation
[N+:1]([C:4]1[C:5]([C:14]#[N:15])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].S(=O)(=O)(O)[OH:17]>>[N+:1]([C:4]1[C:5]([C:14]([NH2:15])=[O:17])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 453821473-Nitro-5-(trifluoromethyl)picolinonitrile

Product 1

HCID 867281553-Nitro-5-(trifluoromethyl)picolinamideYield 86.4%

Conditions

Temperature
60 °C

Procedure

A round bottom flask was charged with 3-nitro-5-(trifluoromethyl)picolinonitrile (910 mg, 4.19 mmol) and sulfuric acid (4192 μl, 4.19 mmol), and the mixture was stirred at 60° C. for 16 h. Upon cooling to RT the crude mixture was poured onto ice, and the resulting solids were filtered, washed with water and dried. 3-nitro-5-(trifluoromethyl)picolinamide (850 mg, 3.62 mmol, 86% yield) was isolated as a light yellow solid. LC/MS (ESI+) m/z=236.1 (M+H).

Workup

  1. additionwas poured onto ice
  2. filtrationthe resulting solids were filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-4b81613331e445a9ad289b2931105533
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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