Reaction equation
[CH2:1]1[C:10]2[C:5]3=[C:6]([CH2:11][CH2:12][CH2:13][N:4]3[C:3](=[O:14])[CH2:2]1)[CH:7]=[CH:8][CH:9]=2.[Br:15]N1C(=O)CCC1=O.O.CC(C)=O.CCOCC>CN(C=O)C>[Br:15][C:8]1[CH:9]=[C:10]2[C:5]3=[C:6]([CH2:11][CH2:12][CH2:13][N:4]3[C:3](=[O:14])[CH2:2][CH2:1]2)[CH:7]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1,2,6,7-tetrahydro-5H-pyrido[3,2,1-ij]quinolin-3-one (9.1 g, 48.6 mmol) in 100 ml dry DMF was added dropwise a solution of N-bromosuccinimide (9.08 g, 51.0 mmol) in 150 ml dry DMF at 0° C. The mixture was stirred at 0° C. for 2 h, then 400 ml water was added and the solution was extracted with ethyl acetate (3×150 ml). The organic phase was washed with water (2×200 ml), then dried over MgSO4 and evaporated, affording a yellow solid, which was purified by crystallization from acetone/ether providing pure 9-bromo-1,2,6,7-tetrahydro-5H-pyrido[3,2,1-ij]quinolin-3-one (6.53, 24.5 mmol, 50%) as pale yellow needles.
Workup
- extractionthe solution was extracted with ethyl acetate (3×150 ml)
- washThe organic phase was washed with water (2×200 ml)
- dry with materialdried over MgSO4
- customevaporated
- customaffording a yellow solid, which
Sources & evidence
- ORD record
- ord-8b70a52ca51748fc840115cb32727ed2
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541404B2
Linked notes
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