Methanol → HCID 18760186, compound

HRID 432685Notes

Reaction equation

HRID 432685 reaction equation
Br.Br[CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[O:10]([C:17]1[C:26]2[N:27]=[CH:28][N:29]([CH2:30][CH2:31][OH:32])[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[Na+].CO>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCl.O>[O:10]([C:17]1[C:26]2[N:27]=[CH:28][N:29]([CH2:30][CH2:31][O:32][CH2:3][C:4]3[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=3)[C:25]=2[C:24]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N:18]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 18760167HCID 18760167, compound

Product 1

HCID 18760186HCID 18760186, compoundYield 81.5%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

3-(Bromomethyl)pyridine hydrobromide (0.638 g, 2.52 mmol) was added in a single portion with stirring to a solution containing 2-(4-phenoxy-1H-imidazo[4,5-c]quinolin-1-yl)ethanol (0.7 g, 2.29 mmol), benzyltrimethylammonium chloride (0.03 g), sodium hydroxide (28 mL of 50%) and dichloromethane (28 mL). After 3 hours analysis by TLC (5% methanol in dichloromethane) indicated that the reaction was complete. The reaction mixture was diluted with water (100 mL) and dichloromethane (100 mL). The layers were separated and the aqueous fraction was extracted with dichloromethane (100 mL). The organic fractions were combined, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure to provide a dark yellow solid. This material was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane) to provide 0.74 g of 4-phenoxy-1-[2-(pyridin-3-ylmethoxy)ethyl]-1H-imidazo[4,5-c]quinoline as a bright yellow solid.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous fraction was extracted with dichloromethane (100 mL)
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a dark yellow solid
  7. customThis material was purified by flash chromatography (silica gel eluting with 5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-d2c78d7ab5d043bd95701a1184c1965c
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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