Sodium Hydroxide → 4-Chloro-6-methylquinoline
Reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6][C:5]2=O.[OH-].[Na+].P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[CH:3]=2)[N:8]=[CH:7][CH:6]=1Participants
4
Procedure
6-Methyl-(1H)-quinolin-4-one (1.57 g, 9.7 mmol) in 20 mL phosphorus oxychloride is heated to 110° C. for 4 hours. The mixture is cooled to room temperature then diluted with ice water (˜200 mL) and the pH is adjusted to ca. 10 by the slow addition of 10 N NaOH, The aqueous solution is extracted with methylene chloride (4×250 mL) and the combined organic layers washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue is filtered through silica gel with 33% EtOAc/hexanes to give the product (1.05 g, 5.9 mmol) as a yellow solid.
Workup
- extractionThe aqueous solution is extracted with methylene chloride (4×250 mL)
- washthe combined organic layers washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- filtrationThe crude residue is filtered through silica gel with 33% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-ef57d5d77a4c4837a34bd7d993f9c951
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06602864B1
Reaction notes
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