Azane;hydrate → 6-Amino-5-methyl-2-pyridinecarboxamide

HRID 541425Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8](=N)[NH2:9])[CH:5]=[CH:4][C:3]=1[CH3:11].[NH3:12].[OH2:13]>[O-]S([O-])(=O)=O.[Cu+2]>[NH2:12][C:2]1[N:7]=[C:6]([C:8]([NH2:9])=[O:13])[CH:5]=[CH:4][C:3]=1[CH3:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Into a 50-mL sealed tube, was placed a solution of 6-bromo-5-methylpicolinimidamide (compound 350.3, 800 mg, 3.74 mmol, 1.00 equiv) and CuSO4 (80 mg) in NH3.H2O (40 mL). The resulting mixture was stirred overnight at 80° C. behind a blast shield. After cooling to ambient temperature, the mixture was then extracted with 2×50 mL of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 750 mg (crude) of the title compound as a brown solid.

Workup

customInto a 50-mL sealed tube
temperatureAfter cooling to ambient temperature
extractionthe mixture was then extracted with 2×50 mL of ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-567d10ed485044d3a4e9b7671c861144
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871790B2

Reaction notes

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