Nitric Acid → 6-nitro-3-(N-propionyl-N-n-propylamino)chroman
Reaction equation
[C:1]([N:5]([CH:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[O:11][CH2:10]1)[CH2:6][CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3].[N+:19]([O-])([OH:21])=[O:20].S(=O)(=O)(O)O>[N+](C)([O-])=O>[N+:19]([C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][CH2:10][CH:9]([N:5]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:6][CH2:7][CH3:8])[CH2:18]2)([O-:21])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To an ice cool solution of 730 mg (2.96 mmol) 3-(N-propionyl-N-n-propylamino)chroman (16) in nitromethane (15 ml) was a mixture of fuming nitric acid (0.70 ml) and concentrated sulphuric acid (1.42 ml) added. The solution was stirred for 90 min at 0° C. The reaction mixture was poured out on ice and the product was extracted with dichloromethane. The organic layer was washed with water and 5% aqueous Na2CO3. The organic layer was separated, dried (MgSO4) and the solvent was evaporated yielding 700 mg (81%) of 6-nitro-3-(N-propionyl-N-n-propylamino)chroman (17).
Workup
- additionadded
- additionThe reaction mixture was poured out on ice
- extractionthe product was extracted with dichloromethane
- washThe organic layer was washed with water and 5% aqueous Na2CO3
- customThe organic layer was separated
- dry with materialdried (MgSO4)
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-4658c602a1384864855ffa7067249fa4
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650427
Reaction notes
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