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

HRID 2351570Notes

Reaction equation

HRID 2351570 reaction equation
[C:1]([C:3]1[C:8]([CH3:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].S(=O)(=O)(O)[OH:11].[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:11])([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

2-cyano-3-methyl pyridine (400g) is suspended in t-butyl alcohol (800 mL) and the mixture heated to 70° C. Concentrated sulphuric acid (400 mL) is added dropwise over 45 minutes. The reaction is complete after a further 30 minutes at 75° C. The mixture is then diluted with water (400 mL), charged with toluene (600 mL) and brought to pH 10 with concentrated aqueous ammonia. The temperature is kept at 50°-55° C. during the work up. The toluene phase is separated, the aqueous layer re-extracted and the combined toluene phases are washed with water. Removal of the toluene yields an oil from which solid product may crystallize. Product yield of 97% determined by internal standard assay on gas chromatograph.

Workup

  1. customis kept at 50°-55° C. during the work
  2. customThe toluene phase is separated
  3. extractionthe aqueous layer re-extracted
  4. washthe combined toluene phases are washed with water
  5. customRemoval of the toluene
  6. customyields an oil from which solid product
  7. custommay crystallize

Sources & evidence

ORD record
ord-4cde268d1b0e4afcbb1a85ba76932f73
Source dataset
uspto-grants-1989_10
Patent number
US04873335

Reaction notes

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