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

HRID 1600994Notes

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

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

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

Sources & evidence

ORD record: ord-300c0485ad84446b96100debd13fcf8d
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977128

Reaction notes

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