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

HRID 1356534Notes

Reaction equation

HRID 1356534 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-11b34984f85747089e9d86fa6f5c21c0
Source dataset
uspto-grants-2003_07
Patent number
US06586595B2

Reaction notes

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