Nitric Acid → HCID 22629541, compound
Reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][C:6]12[CH2:17][CH2:16][CH2:15][C:13]3[C:14]1=[C:9]([CH:10]=[CH:11][CH:12]=3)[NH:8][C:7]2=[O:18].C(OC(=O)C)(=O)C.[N+:26]([O-])([OH:28])=[O:27]>C(O)(=O)C>[N+:26]([C:12]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:18])[C:6]3([CH2:5][CH2:4][CH2:3][CH2:2][Br:1])[CH2:17][CH2:16][CH2:15][C:13]=1[C:14]=23)([O-:28])=[O:27]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 15 °C
Procedure
A 100 mg (0.32 mmol) portion of 2a-(4-bromobutyl)-2a,3,4,5-Tetrahydrobenz [cd] indole-2 (1H) -one was dissolved in 2 ml of acetic acid, and the resulting solution was cooled to 15° C. Thereto was added acetic acid solution (1 ml) containing 46 al (0.48 mmol) of acetic anhydride and 19 μl (0.48 mmol) of nitric acid, and the mixture was stirred overnight at 15° C. The reaction solution was extracted with chloroform and washed with water and sodium bicarbonate aqueous solution in that order. After drying (Na2SO4), the solvent was evaporated under a reduced pressure, and the resulting residue was purified by a silica gel column chromatography (20 cc; elution with ethyl acetate-hexane=1:2) to obtain 83 mg of the title compound (73% in yield). 1H-NMR (CDCl3): δ 1.25 (1 H, m), 1.46 (2 H, m), 1.73-2.02 (5 H, m), 2.18 (2 H, m), 3.24 (2 H, m), 3.33 (2 H, t), 6.89 (1 H, d), 8.15 (1 H, d), 9.07 (1 H, s). EI m/z 352, 354 (1:1) (M+H)+
Workup
- extractionThe reaction solution was extracted with chloroform
- washwashed with water and sodium bicarbonate aqueous solution in that order
- dry with materialAfter drying (Na2SO4)
- customthe solvent was evaporated under a reduced pressure
- customthe resulting residue was purified by a silica gel column chromatography (20 cc; elution with ethyl acetate-hexane=1:2)
Sources & evidence
- ORD record
- ord-064a96c1057641828ec21c34ced00c35
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06355642B1
Reaction notes
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