4-Nitrophenol → Quinoline, 6-fluoro-8-nitro-
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.[N+]([C:15]1[CH:20]=CC(O)=C[CH:16]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1)[N:8]=[CH:20][CH:15]=[CH:16]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
4-Fluoro-2-nitro-phenylamine (15 g, 96 mmol) was added to a mixture of 4-nitrophenol (9.5 g, 144 mmol) and glycerol (27 ml), then concentrated sulphuric acid (8.3 ml, 154 mmol) was added dropwise. The mixture was stirred at 130° C. for 4 hours. For the workup, the reaction mixture was cooled to room temperature, then poured into ice-water. The precipitate was filtered and the aqueous phase was made basic with sodium hydroxide (15% solution). There were obtained 2.0 g (11%) of 6-fluoro-8-nitro-quinoline as a brown solid; (calculated) C9H5FN2O2 [192.2]; (found) [M+H]+=193.
Workup
- temperatureFor the workup, the reaction mixture was cooled to room temperature
- filtrationThe precipitate was filtered
Sources & evidence
- ORD record
- ord-c20fc0e5f2e84417a5fcb5fd2293b50e
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242943B2
Reaction notes
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