Sodium Hydroxide → 2-Chloro-5,6,7,8-tetrahydroquinolin-5-one
Reaction equation
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:11])[C:5]=2[CH:4]=[CH:3][C:2]1=O.P(Cl)(Cl)([Cl:15])=O.[OH-].[Na+]>C(#N)C>[Cl:15][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:11])[CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a suspension of 7,8-dihydroquinoline-2,5(1H,6H)-dione (1.5 g, 9.19 mmol) in acetonitrile (22 mL) was added dropwise phosphorous oxychloride (1.714 mL, 18.39 mmol). The resulting solution was heated to 100° C. and stirred for 2 h. The reaction was cooled to RT and poured into ice-cold water. After basifying the mixture with 2 M sodium hydroxide solution it was extracted with ethyl acetate (3×). After each extraction the pH of the aqueous phase was checked and if necessary adjusted by adding 1 M sodium hydroxide solution. The combined organic layers were dried over sodium sulfate, filtered, and evaporated to dryness. The crude was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate) yielding a colourless solid. Amount 1.23 g. Yield 74%.
Workup
- temperatureThe reaction was cooled to RT
- additionpoured into ice-cold water
- extractionwas extracted with ethyl acetate (3×)
- extractionAfter each extraction the pH of the aqueous phase
- additionby adding 1 M sodium hydroxide solution
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe crude was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate)
- customyielding a colourless solid
Sources & evidence
- ORD record
- ord-1a67f522bbb749f4be1af99a65e031e0
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266855B2
Reaction notes
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