Sodium Hydroxide → 2-Chloro-6-fluoroquinoline
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[CH:6]=[CH:5]2.P(Cl)(Cl)([Cl:15])=O.[OH-].[Na+]>C1(C)C=CC=CC=1>[Cl:15][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=2)[N:8]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
A mixture of 6-fluoroquinolin-2(1H)-one from Step C, (0.971 g, 6 mmol), phosphorous oxychloride (2.83 mL, 30 mmol), and toluene (20 mL) is heated at 95° C. for 2 hours. The reaction is cooled in an ice bath and basified with 50% aqueous sodium hydroxide. The mixture is extracted with ethyl acetate and the extracts are dried over anhydrous magnesium sulfate, filtered, and concentrated to an orange solid (1.01 g). The residue is flash chromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane to provide the title compound as a light pink solid, m.p. 99–101° C.
Workup
- temperatureThe reaction is cooled in an ice bath
- extractionThe mixture is extracted with ethyl acetate
- dry with materialthe extracts are dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated to an orange solid (1.01 g)
- customchromatographed on silica gel Merck-60 with 5% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-db4f91d21adc4a57b597d344b7604f66
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153849B2
Reaction notes
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