Potassium Carbonate → HCID 86626169, compound

HRID 598352Notes

Reaction equation

HRID 598352 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-69e027d1558f4dffbf6e0576409509f4
Source dataset
uspto-grants-2011_03
Patent number
US07897597B2

Reaction notes

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