Sulfuric Acid → 3-Amino-6-(trifluoromethyl)picolinamide

HRID 1016192Notes

Reaction equation

HRID 1016192 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:10]([F:13])([F:12])[F:11])=[N:6][C:7]=1[C:8]#[N:9].S(=O)(=O)(O)[OH:15]>>[NH2:1][C:2]1[C:7]([C:8]([NH2:9])=[O:15])=[N:6][C:5]([C:10]([F:13])([F:11])[F:12])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 573645173-Amino-6-(trifluoromethyl)picolinonitrile

Product 1

HCID 578899673-Amino-6-(trifluoromethyl)picolinamide

Conditions

Temperature
70 °C

Procedure

7 g (0.0374 mol, 1 eq) of 5-amino-6-cyano-2-(trifluoromethyl)pyridine dissolved in 106 ml of 90% sulfuric acid was and heated at 70° C. for 3 h. The reaction mixture was cooled to RT and quenched with ice water and extracted with ethyl acetate. The organic layer was washed with brine and concentrated. The solid product obtained was washed with to get 6.8 g (89.47%) of off white solid. 1H NMR (CDCl3, 400 MHz) 5.5 (1H, bs), 7.1 (1H, d), 7.53 (1H, d), 7.80 (1H, bs). MS 206 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. customquenched with ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. concentrationconcentrated
  6. customThe solid product obtained
  7. washwas washed with
  8. customto get 6.8 g (89.47%) of off white solid

Sources & evidence

ORD record
ord-2f4895a0831546f3b316c1377eb2d52b
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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