Trifluoroacetic acid → 5-Bromo-6-methylpicolinamide

HRID 1401212Notes

Reaction equation

HRID 1401212 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[N:10])=[N:6][C:7]=1[CH3:8].C(O)(C(F)(F)F)=[O:12]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([NH2:10])=[O:12])=[N:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 498187795-Bromo-6-methylpyridine-2-carbonitrile

Product 1

HCID 666077245-Bromo-6-methylpicolinamideYield 54%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 5-bromo-6-methylpicolinonitrile (1.8 g, 9.14 mmol) in a mixture of TFA and sulfuric acid (30 mL, 4:1, V/V) was stirred at 40° C. for 16 h. The reaction mixture was poured into ice water. The resulting solid was filtered off and washed with water and dried to give the desired product as a white solid (1.0 g, 4.65 mmol, 54% yield). MS (ESI) m/z 217.1 [M+2]+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d2ade860c462460a948a4b5639c0c91b
Source dataset
uspto-grants-2014_12
Patent number
US08907087B2

Reaction notes

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