Sulfuric Acid → N-tert-Butyl-3-methylpyridine-2-carboxamide

HRID 986712Notes

Reaction equation

HRID 986712 reaction equation
[C:1](O)([CH3:4])([CH3:3])[CH3:2].[CH3:6][C:7]1[C:8]([C:13]#[N:14])=[N:9][CH:10]=[CH:11][CH:12]=1.S(=O)(=O)(O)[OH:16].[OH-].[Na+]>C(O)(=O)C.O>[C:1]([NH:14][C:13]([C:8]1[C:7]([CH3:6])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 6386tert-ButanolHCID 14798Sodium HydroxideHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideYield 86.7%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

111 g (1.5 mol) of tert.-butanol and 118 g (1 mol) of 3-methyl-2-cyanopyridine in 100 ml of glacial acetic acid are initially taken. 147 g of sulphuric acid (100% strength) are added dropwise to this mixture at 50° C. in the course of 0.5 hours, and the mixture is stirred for 3 hours at 50° C. The oil is stirred into 1,000 ml of water, and the resulting solution is adjusted to pH 7 with concentrated sodium hydroxide solution, while cooling with ice. The oil which separates out is separated off, taken up in methylene chloride and extracted by shaking with water. The organic phase is dried over sodium sulphate, evaporated down and distilled. 166.5 g (86.7% of theory) of 3-methylpyridine-2-carboxylic acid N-tert.-butylamide are obtained as a viscous oil of boiling point 155° C./4 mbar.

Workup

  1. temperaturewhile cooling with ice
  2. customThe oil which separates out is separated off
  3. extractionextracted
  4. stirringby shaking with water
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. customevaporated down
  7. distillationdistilled

Sources & evidence

ORD record
ord-0fc6091f655547b8bc1c3ba67b77918b
Source dataset
uspto-grants-1987_12
Patent number
US04715888

Reaction notes

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