Hydrochloric Acid → 4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium
Reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N+]([O-])=O)[C:5]([CH3:12])=[CH:4][N+:3]=1[O-:13].[ClH:14].C(=O)([O-])[O-].[K+].[K+]>O.CN(C)C=O>[Cl:14][C:6]1[C:5]([CH3:12])=[CH:4][N+:3]([O-:13])=[C:2]([CH3:1])[C:7]=1[CH3:8]Participants
Conditions
- Temperature
- 100 °C
Procedure
2,3,5-trimethyl-4-nitropyridine 1-oxide (850 g, 4.67 mol) was charged with water (400 g) and 36% concentrated hydrochloric acid (1.69 kg), and the resultant solution was heated to 70° C. The solution was then charged with N,N-dimethylformamide (115 mL) and heated to 100° C. Once the reaction had finished, the solution was cooled to 20° C. and then charged into a mixture of potassium carbonate (1.40 kg) and water (7 L). The resultant mixture was extracted with chloroform (1.0 L×3), dried over sodium sulfate and then concentrated. The resultant crude product was stirred for 2 hours in a mixed solution of diisopropyl ether (500 mL) and n-hexane (1.0 L), and the resultant solution was then filtered with suction. The resultant wet substance was dried overnight under vacuum to obtain 666.4 q of the title compound.
Workup
- temperaturethe solution was cooled to 20° C.
- extractionThe resultant mixture was extracted with chloroform (1.0 L×3)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- filtrationthe resultant solution was then filtered with suction
- customThe resultant wet substance was dried overnight under vacuum
Sources & evidence
- ORD record
- ord-78267d0e838d43c9ae359bcc13792a2a
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09040564B2
Reaction notes
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