Benzyl Bromide → 1-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

HRID 1267841Notes

Reaction equation

HRID 1267841 reaction equation
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13].CC(C)([O-])C.[K+].C1COCC1.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.O.C(OC)(C)(C)C>[CH2:25]([N:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH2:4][N:3]3[C:2]1=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 127895324H-Imidazo[4,5,1-ij]quinolin-2(1H)-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 97952141-Benzyl-4H-imidazo[4,5,1-ij]quinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A mixture of 4H-imidazo[4,5,1-ij]quinolin-2(1H)-one (I, J. Heterocyclic Chem., 19, 837-49 (1982), 1.0 g, 5.8 mmol) in DMF (10 ml) is cooled to 0° and treated with potassium t-butoxide in THF (1.98 M, 3.2 ml, 6.3 mmol) maintaining the reaction temperature at 0°. The resulting mixture is stirred at 0° for 10 minutes. Benzyl bromide (0.73 ml, 6.1 mmol) is then added while maintaining the reaction temperature at methyl t-butyl ether (MTBE) from water followed by several water washes. The MTBE phase is concentrated under reduced pressure. The concentrate is cooled to 0°, filtered and washed two times with 0° MTBE. The product is dried at 50° under reduced pressure with a nitrogen purge to give the title compound, CMR (CDCl3, 100 MHz) 153.78, 136.44, 128.69, 127.67, 127.60, 126.73, 125.86, 122.90, 122.78, 121.28, 116.92, 116.17, 108.36, 44.95 and 42.37 δ.

Workup

  1. temperatureis cooled to 0°
  2. temperaturemaintaining the reaction temperature at 0°
  3. concentrationThe MTBE phase is concentrated under reduced pressure
  4. temperatureThe concentrate is cooled to 0°
  5. filtrationfiltered
  6. washwashed two times with 0° MTBE
  7. customThe product is dried at 50° under reduced pressure with a nitrogen
  8. custompurge

Sources & evidence

ORD record
ord-a6413ad9201140f19789094c2e4632e6
Source dataset
uspto-grants-2003_04
Patent number
US06555548B2

Reaction notes

Loading…