Methanol → HCID 18760167, compound

HRID 432684Notes

Reaction equation

HRID 432684 reaction equation
OS(C(F)(F)F)(=O)=O.C([O:16][CH2:17][CH2:18][N:19]1[C:31]2[C:30]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[N:24]=[C:23]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:22]=2[N:21]=[CH:20]1)C1C=CC=CC=1.CO.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[O:32]([C:23]1[C:22]2[N:21]=[CH:20][N:19]([CH2:18][CH2:17][OH:16])[C:31]=2[C:30]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[N:24]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 62406Trifluoromethanesulfonic acidHCID 18760196HCID 18760196, compound

Product 1

HCID 18760167HCID 18760167, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Procedure

Under a nitrogen atmosphere, triflic acid (29.0 g) was added dropwise to a solution of 1-[2-(benzyloxy)ethyl]-4-phenoxy-1H-imidazo[4,5-c]quinoline (7.65 g) in anhydrous dichloromethane (200 mL). When analysis by TLC (5% methanol in dichloromethane) indicated that the reaction was complete, the reaction mixture was concentrated under reduced pressure to provide an oil. This material was dissolved in ethyl acetate and then combined with triethylamine (10 eq.). The solution was diluted with additional ethyl acetate, washed with water, washed with brine, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to provide ˜4.8 g of 2-(4-phenoxy-1H-imidazo[4,5-c]quinolin-1-yl)ethanol as a white fluffy solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto provide an oil
  3. washwashed with water
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-bdd37f65385145f0a48168f2fb706d2d
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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