Nitric Acid → 2,6-Dichloro-3-methyl-5-nitropyridine

HRID 1888003Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[N:3]=1.[N+:10]([O-])([OH:12])=[O:11].[OH-].[Na+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[C:4]([Cl:9])[N:3]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2,6-dichloro-3-methylpyridine (2.20 g, 13.6 mmol) in concentrated sulfuric acid (11.3 mL) was treated with fuming nitric acid (6.65 mL) and heated to 110° C. for 3 hours. The reaction mixture was poured into ice-water and neutralized with 2N sodium hydroxide. The mixture was extracted with dichloromethane (3×70 mL) and the combined extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to yield 2,6-dichloro-3-methyl-5-nitropyridine (2.43 g, 86%). 400 M Hz 1H NMR (DMSO-d6) δ: 8.66 (s, 1H), 2.39 (s, 3H).

Workup

extractionThe mixture was extracted with dichloromethane (3×70 mL)
dry with materialthe combined extracts were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-cd1dcc60bc014ac09efbaf37aebd3954
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501770B2

Reaction notes

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