Benzyl Bromide → HCID 14171579, compound

HRID 2291988Notes

Reaction equation

HRID 2291988 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[N:8]([CH:12]=[CH:13][CH:14]=3)[NH:9][C:10]=2[CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CC(=O)CC>[CH2:22]([N:9]1[C:10]2[CH:11]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[C:6](=[O:15])[C:7]2=[CH:14][CH:13]=[CH:12][N:8]12)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 14171570HCID 14171570, compound

Product 1

HCID 14171579HCID 14171579, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a slurry of 7-chloropyrrolo[1,2-b]cinnolin-10(5H)-one (35.0 g) and potassium carbonate (66.34 g) in 150 ml of 2-butanone was added benzyl bromide (44.47 g) and the mixture was stirred at 50° for 2 h. The reaction was quenched with 750 ml of H2O, mixture was neutralized with 2N HCl to pH 8 and extracted with chloroform. The organic layer was washed successively with dilute HCl, H2O and brine and thereafter dried (MgSO4), charcoaled, filtered and concentrated. The yellow-orange residue was purified by flash chromatography (silica, dichloromethane) and recrystallized from ethanol to give 2.0 g of light yellow microcrystals, mp 163°-165°.

Workup

  1. customThe reaction was quenched with 750 ml of H2O, mixture
  2. extractionextracted with chloroform
  3. washThe organic layer was washed successively with dilute HCl, H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe yellow-orange residue was purified by flash chromatography (silica, dichloromethane)
  8. customrecrystallized from ethanol
  9. customto give 2.0 g of light yellow microcrystals, mp 163°-165°

Sources & evidence

ORD record
ord-984a79c3e06c414892441c49644b194c
Source dataset
uspto-grants-1989_01
Patent number
US04800203

Reaction notes

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