Quinoline → 2-chloro-3-nitro-6-(trifluoromethyl)pyridine
Reaction equation
P(Cl)(Cl)([Cl:3])=O.N1C2C(=CC=CC=2)C=CC=1.[N+:16]([C:19]1[C:20](=O)[NH:21][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:23][CH:24]=1)([O-:18])=[O:17].C(=O)(O)[O-].[Na+]>O>[Cl:3][C:20]1[C:19]([N+:16]([O-:18])=[O:17])=[CH:24][CH:23]=[C:22]([C:25]([F:28])([F:27])[F:26])[N:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
To phosphorous oxychloride (11 ml, 117 mmol) was added quinoline (8.4 ml, 70 mmol) followed by 3-nitro-6-trifluoromethyl-2(1H)-pyridone (24.0 g, 115 mmol), and the resulting solution heated at 140° C. for 18 h. The solution was then cooled to 100° C., when water (50 ml) was carefully added. After cooling to room temperature, saturated sodium bicarbonate (200 ml) was added and the mixture extracted with ethyl acetate (2×200 ml). The extracts were dried (MgSO4) and concentrated, and the residue purified by silica chromatography to give the product as a brown oil (22.7 g, 0.1 mol, 87% yield).
Workup
- temperatureThe solution was then cooled to 100° C.
- temperatureAfter cooling to room temperature
- extractionthe mixture extracted with ethyl acetate (2×200 ml)
- dry with materialThe extracts were dried (MgSO4)
- concentrationconcentrated
- customthe residue purified by silica chromatography
Sources & evidence
- ORD record
- ord-35381bdad3914366a6625137a0539360
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225320B1
Reaction notes
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