Citric Acid → 4-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol

HRID 388611Notes

Reaction equation

HRID 388611 reaction equation
[OH-].[Na+].N1(C([O:10][CH2:11][CH2:12][CH2:13][N:14]2[C:26]3[C:25]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[N:19]=[C:18]([Cl:27])[C:17]=3[N:16]=[C:15]2[OH:28])=O)C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[Cl:27][C:18]1[C:17]2[N:16]=[C:15]([OH:28])[N:14]([CH2:13][CH2:12][CH2:11][OH:10])[C:26]=2[C:25]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[N:19]=1

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 178525476HCID 178525476, compound

Product 1

HCID 1785208234-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-olYield 864.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (700 mL of 2 N) was added to a stirred suspension of 3-(4-chloro-2-hydroxy-1H-imidazo[4,5-c]quinolin-1-yl)propyl 1H-imidazole-1-carboxylate (38 g, 0.010 mol) in methanol (100 mL), and the resulting solution was stirred for two hours at room temperature and then adjusted to pH 7 with the addition of 10% w/w aqueous citric acid. A precipitate formed, and the mixture was stirred overnight. The precipitate was isolated by filtration and washed with acetonitrile to provide 24 g of 4-chloro-1-(3-hydroxypropyl)-1H-imidazo[4,5-c]quinolin-2-ol.

Workup

  1. customA precipitate formed
  2. stirringthe mixture was stirred overnight
  3. customThe precipitate was isolated by filtration
  4. washwashed with acetonitrile

Sources & evidence

ORD record
ord-36119a9f6943427894a69eecb5fbf29c
Source dataset
uspto-grants-2013_02
Patent number
US08377957B2

Reaction notes

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