Nitric Acid → 4-Nitro-5,6,7,8-tetrahydroquinoline 1-oxide
Reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[N+:10]1([O-:20])[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][C:14]=2[CH:13]=[CH:12][CH:11]=1>O>[N+:6]([C:13]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:19]=2[N+:10]([O-:20])=[CH:11][CH:12]=1)([O-:9])=[O:7]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred mixture of sulphuric acid (200 ml) and nitric acid (200 ml) was treated with 5,6,7,8-tetrahydroquinoline N-oxide (47 g, 315 mmol), heated at 60°-80° for 3h, cooled to room temperature, poured onto ice (1 Kg), diluted with water (1 1), and extracted with dichloromethane (3×500 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give the product (48 g) as an oil.
Workup
- additionpoured onto ice (1 Kg)
- extractionextracted with dichloromethane (3×500 ml)
- dry with materialThe extracts were dried (MgSO4)
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-333db474aa3a47a6a6674157e1b80fc2
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194439
Reaction notes
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