Water → 8-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

HRID 44178

Reaction equation

HRID 44178 reaction equation
[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][C:4](=[O:13])[N:3]3[CH2:2]1.[Br:14]N1C(=O)CCC1=O.O.CC(C)=O.CCOCC>CN(C=O)C>[Br:14][C:9]1[CH:8]=[C:7]2[C:12]3=[C:11]([CH2:1][CH2:2][N:3]3[C:4](=[O:13])[CH2:5][CH2:6]2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67184N-bromobutanimideHCID 91665PyroquilonHCID 21584533Acetone diethylether

Product 1

HCID 529370408-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (10.0 g, 55.8 mmol) in 100 ml dry DMF was added dropwise a solution of N-bromosuccinimide (10.4 g, 58.6 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 8-bromo-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (12.8 g, 50.8 mmol, 91%) as pale yellow needles.

Workup

  1. extractionthe solution was extracted with ethyl acetate (3×150 ml)
  2. washThe organic phase was washed with water (2×200 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customaffording a yellow solid, which

Sources & evidence

ORD record
ord-1fe1bbdfc69249af832a95826a35b617
Source dataset
uspto-grants-2013_09
Patent number
US08541404B2

Linked notes

Loading…