4-Toluenesulfonyl chloride → HCID 21984131, compound

HRID 9453Notes

Reaction equation

HRID 9453 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:13]=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.ClC1C=C(C=CC=1)C(OO)=O.[OH-].[NH4+:31].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(#N)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH:16]([CH3:18])[CH3:17])[CH:13]=[N:12][C:7]=3[C:8]([NH2:31])=[N:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 219841367-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline

Product 1

HCID 21984131HCID 21984131, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The method described in Part J of Example 365 was used to oxidize and aminate 7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinoline (18.7 g, 58.4 mmol). 3-Chloroperoxybenzoic acid (22.1 g of 50% pure material, 129 mmol) was added in five portions during the oxidation step, and the amination with ammonium hydroxide (146 mL) and p-toluenesulfonyl chloride (16.6 g, 87.6 mmol) proceeded overnight. The crude product was obtained as an oil, which was treated with acetonitrile to form a precipitate. The precipitate was isolated by filtration, washed with a small amount of acetonitrile, and recrystallized from acetonitrile to provide 4 g of 7-bromo-1-(2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine as off-white needeles, mp 218–220° C.

Workup

  1. customThe crude product was obtained as an oil, which
  2. customto form a precipitate
  3. customThe precipitate was isolated by filtration
  4. washwashed with a small amount of acetonitrile
  5. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-755d4f9ae9fc48b3bfbb003cb502e6b9
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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