Ammonia → N-tert-Butyl-3-methylpyridine-2-carboxamide

HRID 2133

Reaction equation

HRID 2133 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[OH:10]S(O)(=O)=O.[C:15]1([CH3:21])[CH:20]=CC=C[CH:16]=1.N>C(O)(C)(C)C.O>[CH3:16][C:15]([NH:2][C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)=[O:10])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 1140TolueneHCID 8199283-Methylpyridine-2-carbonitrile

Product 1

HCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
70 °C

Procedure

Suspend 2-cyano-3-methyl pyridine (400 g) in t-butanol (800 mL) and heat to 70° C. Add concentrated H2SO4 (400 mL) dropwise over 45 minutes. Maintain the temperature at 75° C., until the reaction is complete, and for an additional 30 minutes. Dilute the mixture with water (400 mL), charge with toluene (600 mL) and bring to pH 10 with concentrated aqueous ammonia. Maintain the temperature at 50°-55° C. during the work up. Separate the toluene phase, and reextract the aqueous layer. Combine toluene phases and wash with water. Remove the toluene to yield the title compound N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide, as an oil, from which solid product is crystallized. (Yield 97%, as determined by an internal standard assay with gas chromatography).

Workup

  1. temperatureMaintain the temperature at 75° C.
  2. temperatureMaintain the temperature at 50°-55° C. during the work up
  3. customSeparate the toluene phase
  4. washCombine toluene phases and wash with water
  5. customRemove the toluene

Sources & evidence

ORD record
ord-07e514fe010d477b830fbb79e7963a40
Source dataset
uspto-grants-1998_03
Patent number
US05728703

Linked notes

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