HCID 178471911, compound → 3-acetyl-8-bromoquinolin-4(1H)-one
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH:9]=[C:10]([C:16](=[O:18])[CH3:17])[C:11]([O:13]CC)=O>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[C:16]([C:10]1[C:11](=[O:13])[C:4]2[C:3](=[C:2]([Br:1])[CH:7]=[CH:6][CH:5]=2)[NH:8][CH:9]=1)(=[O:18])[CH3:17]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 250 °C
Procedure
To Dowtherm (20 ml) at apx 200° C. was added solid ethyl 2-(((2-bromophenyl)amino) methylene)-3-oxobutanoate (3 g, 9.61 mmol). The reaction was heated to 250° C. and stirred for 1 h. LCMS showed consumption of starting material and formation of desired product along with an unknown biproduct of lower mass. The reaction was allowed to cool to room temperature and was them poured into 150 mL of hexanes. The mixture was stirred for 15 min, then the precipitate was collected by filtration and dried to afford 3-acetyl-8-bromoquinolin-4(1H)-one (1.77 g, 6.65 mmol, 69.2% yield) as a light brown solid. LCMS: (M+H)+: 265.9.
Workup
- customconsumption of starting material and formation of desired product along with an unknown biproduct of lower mass
- temperatureto cool to room temperature
- additionpoured into 150 mL of hexanes
- stirringThe mixture was stirred for 15 min
- filtrationthe precipitate was collected by filtration
- customdried
Sources & evidence
- ORD record
- ord-4fbf0b508d8c4f9f8f7a7097baae80e3
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340556B2
Reaction notes
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