Nitric Acid → 6-Nitro-3,4-dihydroquinolin-2(1H)-one
Reaction equation
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][C:2]1=[O:11].O.[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][C:2](=[O:11])[CH2:3][CH2:4]2)([O-:15])=[O:14]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
3,4-Dihydro-1H-quinolin-2-one (7.2 g, 48.9 mmol) was dissolved in sulfuric acid (150 mL) and cooled to 0° C. Water (35 mL) was added dropwise, followed by nitric acid (3.5 mL, 78 mmol) dropwise following this, retaining temperature below 0° C. The reaction mixture was stirred at 0° C. for 15 min after which LC-MS showed one major peak corresponding to desired product. The reaction mixture was then poured into ice water and extracted with EtOAc (3×); the combined organic phases were dried over MgSO4, filtered and concentrated to afford a brown solid-6-nitro-3,4-Dihydro-1H-quinolin-2-one −8.56 g (91% yield).
Workup
- customtemperature below 0° C
Sources & evidence
- ORD record
- ord-7f820c4359d44d57adbbb89a668a682a
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08697739B2
Reaction notes
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