5,6,7,8-Tetrahydroquinoline-3-carbonitrile → 3-Cyano-5,6,7,8-tetrahydroquinoline 1-oxide
Reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[C:3]([C:11]#[N:12])[CH:2]=1.B1([O-])O[O:14]1.O.O.O.O.[Na+]>C(O)(=O)C>[C:11]([C:3]1[CH:2]=[N+:1]([O-:14])[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=1)#[N:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 5,6,7,8-tetrahydroquinoline-3-carbonitrile (633 mg, 4.00 mmol) in acetic acid (5 ml) at 40° C. was portionwise added sodium perborate tetrahydrate (677 mg, 4.4 mmol) and the mixture was stirred at 40° C. for 16 hours. The acetic acid was removed by evaporation at reduced pressure, the residue was basified with a saturated aqueous solution of sodium hydrogencarbonate, and the mixture extracted thrice with ethyl acetate. The combined extracts were dried over sodium sulphate and the solvent removed in vacuum to give the 3-cyano-5,6,7,8-tetrahydroquinoline 1-oxide (645 mg, 93% yield) as a white solid. MS (ISP): m/z=175.1 [M+H]+.
Workup
- customat 40° C.
- customThe acetic acid was removed by evaporation at reduced pressure
- extractionthe mixture extracted thrice with ethyl acetate
- dry with materialThe combined extracts were dried over sodium sulphate
- customthe solvent removed in vacuum
Sources & evidence
- ORD record
- ord-a0ad7d2214b94894a86e477f38c051e4
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785436B2
Reaction notes
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