2-Amino-6-methoxy-3-nitropyridine → HCID 178419698, compound

HRID 1784790Notes

Reaction equation

[Br:1]C1N=C(N)C([N+]([O-])=O)=CC=1.C[O:13][C:14]1[N:19]=[C:18]([NH2:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][CH:15]=1>Br.C(O)(=O)C>[BrH:1].[NH2:20][C:18]1[N:19]=[C:14]([OH:13])[CH:15]=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

6-Bromo-3-nitro-pyridin-2-ylamine. To a glass pressure vessel containing 6-methoxy-3-nitro-pyridin-2-ylamine (5.0 g, 29.5 mmol) was added 30% hydrogen bromide/acetic acid (60 mL). The vessel was sealed, and the contents were heated to 60° C. for 24 h. The reaction mixture was cooled, and the solvent was removed in vacuo giving 6.8 g (>95%) of crude 6-amino-5-nitro-pyridin-2-ol hydrobromide (HPLC: Rt=5.46). This material (2.0 g, 8.5 mmol) was taken up in toluene (30 mL), followed by phosphorus pentoxide (2.4 g, 17.0 mmol) and tetrabutyl ammonium bromide (3.2 g, 9.7 mmol). The mixture was heated to reflux for 4 h. The reaction mixture was cooled to 0° C., diluted with saturated NaHCO3, and extracted with ethyl acetate (3×100 mL). The combined organics were washed with water (100 mL) and dried (Na2SO4) to afford 1.18 g (64%) of 6-bromo-3-nitro-pyridin-2-ylamine.

Workup

customThe vessel was sealed
temperatureThe reaction mixture was cooled
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-1191f8a6159b4c1689edac52db4be715
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504414B2

Reaction notes

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