Potassium Carbonate → HCID 86626169, compound

HRID 2383180Notes

Reaction equation

HRID 2383180 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]2[N+:20]([O-])=[CH:19][C:18]3[N:25]=[C:26]([CH2:32][O:33][CH3:34])[N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:17]=3[C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:6]([O:13][C:14]1[CH:23]=[CH:22][C:21]2[N:20]=[C:19]([Cl:3])[C:18]3[N:25]=[C:26]([CH2:32][O:33][CH3:34])[N:27]([CH2:28][CH:29]([CH3:31])[CH3:30])[C:17]=3[C:16]=2[CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 67051118HCID 67051118, compound

Product 1

HCID 86626169HCID 86626169, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorous oxychloride (1.78 g, 11.6 mmol) was added dropwise to a solution of 8-benzyloxy-1-(2-methylpropyl)-2-methoxymethyl-5-oxido-1H-imidazo[4,5-c]quinoline in 10 mL of DMF. After 1 hour, the reaction was poured onto 700 mL of ice and stirred overnight. Solid potassium carbonate was then added until the pH of the reached 10. After 30 minutes of stirring, the mixture was filtered. The resulting solid was washed with water and dried under a stream of air to give 3.75 g of 8-benzyloxy-4-chloro-1-(2-methylpropyl)-2-methoxymethyl-1H-imidazo[4,5-c]quinoline as a yellow-tan solid.

Workup

  1. stirringAfter 30 minutes of stirring
  2. filtrationthe mixture was filtered
  3. washThe resulting solid was washed with water
  4. customdried under a stream of air

Sources & evidence

ORD record
ord-4df50bf875d543a5adf379c42698986a
Source dataset
uspto-grants-2012_09
Patent number
US08263594B2

Reaction notes

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