Potassium Carbonate → HCID 66620417, compound

HRID 415516Notes

Reaction equation

HRID 415516 reaction equation
C([O:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH2:22][CH2:23]Cl)C1C=CC=CC=1.B(Br)(Br)Br.C([O-])([O-])=O.[K+].[K+]>ClCCl>[CH:19]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]=1[C:21]1[N:9]3[O:8][CH2:23][CH2:22][C:10]3=[N:11][C:12]=1[CH:13]=[N:14]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 66620013HCID 66620013, compound

Product 1

HCID 66620417HCID 66620417, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 1-(benzyloxy)-2-(2-chloroethyl)-1H-imidazo[4,5-c]quinoline (0.6058 g, 1.793 mmol) in 10 mL of dichloromethane was treated with a 1 M solution of BBr3 in dichloromethane (5.4 mL, 5.379 mmol). After 2 hours, 10 mL of saturated, aqueous K2CO3 solution were added and the reaction mixture stirred under ambient conditions for 3 hrs. The organic portion was separated and washed successively with H2O and brine, dried over Na2SO4, and concentrated under reduced pressure. Chromatography (SiO2, 0-15% CMA/CHCl3) gave 0.0465 g of 8,9-dihydroisoxazolo[2′,3′:1,2]imidazo[4,5-c]quinoline as a tan solid.

Workup

  1. customThe organic portion was separated
  2. washwashed successively with H2O and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0f5bcb08fc7b47478c0715356783d870
Source dataset
uspto-grants-2012_01
Patent number
US08088788B2

Reaction notes

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