Cyanogen Bromide → HCID 86626282, compound

HRID 1097560Notes

Reaction equation

HRID 1097560 reaction equation
[N:1]#[C:2][Br:3].[CH2:4]([NH:11][C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]=[C:14]([Cl:22])[C:13]=1[NH2:23])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)C>[BrH:3].[CH2:4]([N:11]1[C:12]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:15]=[C:14]([Cl:22])[C:13]=2[N:23]=[C:2]1[NH2:1])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 10476Cyanogen Bromide2×HCID 46830486HCID 46830486, compound

Product 1

HCID 86626282HCID 86626282, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Cyanogen bromide (2.2 g, 21 mmol) was added to a solution of N4-benzyl-2-chloroquinoline-3,4-diamine (5.0 g, 17 mmol) in ethanol (50 mL), and the solution was heated at 90° C. for two hours. An analysis by liquid chromatography/mass spectrometry (LC/MS) indicated the presence of starting material. Additional cyanogen bromide (2.2 g, 21 mmol) was added, and the reaction was stirred for one hour at 90° C., stirred for three days at 50° C., and allowed to cool to ambient temperature. The solvent was removed under reduced pressure, and the resulting solid was washed with diethyl ether (1 L) to provide 6.84 g of 1-benzyl-4-chloro-1H-imidazo[4,5-c]quinoline-2-amine hydrobromide as a dark gray powder.

Workup

  1. stirringstirred for three days at 50° C.
  2. temperatureto cool to ambient temperature
  3. customThe solvent was removed under reduced pressure
  4. washthe resulting solid was washed with diethyl ether (1 L)

Sources & evidence

ORD record
ord-fd3a8ae96b3b4182826a910a96d2a1c3
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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