Chloroform → HCID 67273848, compound

HRID 602263Notes

Reaction equation

HRID 602263 reaction equation
[CH2:1]([C:3]1[N:4]([C@@H:16]([CH3:19])[CH2:17][OH:18])[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]=[CH:7][C:6]=2[N:15]=1)[CH3:2].BrN1C(=O)CCC1=O.C(Cl)(Cl)Cl>C(Cl)(Cl)(Cl)Cl>[CH3:2][CH:1]1[C:3]2=[N:15][C:6]3[CH:7]=[N:8][C:9]4[C:14]([C:5]=3[N:4]2[C@@H:16]([CH3:19])[CH2:17][O:18]1)=[CH:13][CH:12]=[CH:11][CH:10]=4

Participants

5

Reactant 3

HCID 6212ChloroformHCID 67184N-bromobutanimideHCID 67273297HCID 67273297, compound

Product 1

HCID 67273848HCID 67273848, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

(2S)-2-(2-Ethyl-1H-imidazo[4,5-c]quinolin-1-yl)propan-1-ol (0.50 g, 1.96 mmol) was suspended in 20 mL of CCl4 under an atmosphere of N2. The mixture was treated with N-bromosuccinimide (0.35 g, 1.96 mmol), heated to reflux, and irradiated with a sunlamp. After ˜20 hours the reaction was allowed to cool to ambient temperature, then it was partitioned between CH2Cl2 and saturated NaHCO3 solution. The layers were separated; the organic layer was washed sequentially with saturated NaHCO3 solution and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a brown foam. Chromatography (AFC, SiO2, 0-15% CMA/CHCl3) gave (11S)-8,11-dimethyl-10,11-dihydro-8H-[1,4]oxazino[4′,3′:1,2]imidazo[4,5-c]quinoline (80 mg) as a light yellow solid.

Workup

  1. temperatureheated
  2. temperatureto reflux
  3. customirradiated with a sunlamp
  4. customit was partitioned between CH2Cl2 and saturated NaHCO3 solution
  5. customThe layers were separated
  6. washthe organic layer was washed sequentially with saturated NaHCO3 solution and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown foam

Sources & evidence

ORD record
ord-cc639989d8f54e0dae4dd4feee677f31
Source dataset
uspto-grants-2011_03
Patent number
US07906506B2

Reaction notes

Loading…