Cyanogen Bromide → HCID 86626274, compound

HRID 1097549Notes

Reaction equation

HRID 1097549 reaction equation
[Cl:1][C:2]1[C:11]([NH2:12])=[C:10]([NH:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:18]#[C:19][Br:20]>C(O)C>[BrH:20].[Cl:1][C:2]1[C:11]2[N:12]=[C:19]([NH2:18])[N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:10]=2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 117470392-Chloro-N~4~-(2-methylpropyl)quinoline-3,4-diamine

Product 1

HCID 86626274HCID 86626274, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-chloro-N4-(2-methylpropyl)-3,4-quinolinediamine (André et al, U.S. Pat. No. 4,988,815, Example 6, 8.92 g, 35.7 mmol) in ethanol (50 mL) was stirred at 100° C.; cyanogen bromide (5.67 g, 53.5 mmol) was added in one portion. The red solution was stirred overnight, washed three times with water, and washed once with brine. A precipitate formed in the aqueous washings and was isolated by filtration. The organic fraction was dried over magnesium sulfate, filtered through a layer of CELITE filer agent, concentrated under reduced pressure, further dried under high vacuum, and combined with the isolated precipitate to provide 9.81 g of 4-chloro-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline-2-amine hydrobromide as a dark red solid.

Workup

  1. washwashed three times with water
  2. washwashed once with brine
  3. customA precipitate formed in the aqueous washings
  4. customwas isolated by filtration
  5. dry with materialThe organic fraction was dried over magnesium sulfate
  6. filtrationfiltered through a layer of CELITE filer agent
  7. concentrationconcentrated under reduced pressure
  8. customfurther dried under high vacuum

Sources & evidence

ORD record
ord-a198fe4280b4467b9588fb7e93c36643
Source dataset
uspto-grants-2012_03
Patent number
US08143270B2

Reaction notes

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