2-Methoxy-3-nitropyridine → 3-Nitropyridin-2-ylamine

HRID 1583650Notes

Reaction equation

CO[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C([O-])(=O)C.[NH4+:16]>O>[N+:9]([C:8]1[C:3]([NH2:16])=[N:4][CH:5]=[CH:6][CH:7]=1)([O-:11])=[O:10]

Participants

Conditions

Temperature: 150 °C

Procedure

One gram (6.5 mmol) of 2-methoxy-3-nitropyridine and 5.0 g (65 mmol) of ammonium acetate were added to a 100 ml round bottom flask. The reaction mixture was heated at 150° C. for approximately 16 hours under an argon atmosphere. An additional 5 g of ammonium acetate was added to the reaction mixture which was allowed to heat for an additional 8 hours. Thin layer chromatography of the mixture indicated that both product and starting material were present. The reaction mixture was cooled and poured into approximately 100 ml of water. The precipitated solid was collected by filtration to provide 209.8 mg of 3-nitro-2-aminopyridine. m/e 139. The NMR spectrum of the collected produot was identical to that of an authentic reference standard.

Workup

temperatureto heat for an additional 8 hours
temperatureThe reaction mixture was cooled
filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record: ord-e31129be2022401db1fa2fb9f0826f72
Source dataset: uspto-grants-1985_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04552967

Reaction notes

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