Sulfuric Acid → 3-Methylpyridine-2-carboxamide

HRID 60789

Reaction equation

HRID 60789 reaction equation
[CH3:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)[OH:11].C([O-])([O-])=O.[Na+].[Na+]>O>[CH3:1][C:2]1[C:3]([C:8]([NH2:9])=[O:11])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 166410233-Methylpyridine-2-carboxamideYield 97%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-methylpicolinonitrile (2.36 g, 20 mmol) and conc. sulfuric acid (12.5 mL) was stirred at 80° C. for 25 min. The solution was cooled to rt, poured into water (80 mL), followed by addition of sat. Na2CO3 (aq.) until pH ˜7. The resulting mixture was extracted with DCM (3×) and the combined organic layer was dried over MgSO4 and concentrated in vacuo to provide 3-methylpicolinamide as a white solid (2.65 g, 97%). 1H NMR (CDCl3, 400 MHz) δ 8.43 (dd, 1H), 7.93 (brs, 1H), 7.62 (dd, 1H), 7.35 (dd, 1H), 5.44 (brs, 1H), 2.76 (s, 3H).

Workup

  1. temperatureThe solution was cooled to rt
  2. extractionThe resulting mixture was extracted with DCM (3×)
  3. dry with materialthe combined organic layer was dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af1e112a241f4df6851c8639a4e9428b
Source dataset
uspto-grants-2016_09
Patent number
US09440982B2

Linked notes

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