Benzyl Bromide → HCID 14171579, compound

HRID 1639254Notes

Reaction equation

HRID 1639254 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, and the 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 12.0 g of light yellow microcrystals, mp 163°-165°.

Workup

  1. customThe reaction was quenched with 750 ml of H2O
  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 12.0 g of light yellow microcrystals, mp 163°-165°

Sources & evidence

ORD record
ord-db9422b6fa5a4f0ab8b48c52d89be2ef
Source dataset
uspto-grants-1989_11
Patent number
US04883794

Reaction notes

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