Acetic Acid → HCID 66649813, compound

HRID 419291Notes

Reaction equation

HRID 419291 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][O:24][Si](C(C)(C)C)(C)C)[C:20]([CH2:32][Cl:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[N:21]([CH2:22][CH2:23][OH:24])[C:20]([CH2:32][Cl:33])=[N:19][C:14]=3[CH:15]=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 66649907HCID 66649907, compound

Product 1

HCID 66649813HCID 66649813, compoundYield 104.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A 500 mL round bottom flask was charged with 7-(benzyloxy)-1-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(chloromethyl)-1H-imidazo[4,5-c]quinoline (30 g, 0.06 mol), acetic acid (300 mL), and water (60 mL). The suspension was heated at 50° C. for 24 hours. The heat was removed and the greenish homogeneous solution was concentrated to dryness. The solid was stirred in diethyl ether (300 mL) for 1 hour, isolated by vacuum filtration, washed with diethyl ether (100 mL), and dried on vacuum funnel to provide 23 g of 2-[7-(benzyloxy)-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethanol as a green solid.

Workup

  1. customThe heat was removed
  2. concentrationthe greenish homogeneous solution was concentrated to dryness
  3. customisolated by vacuum filtration
  4. washwashed with diethyl ether (100 mL)
  5. customdried on vacuum funnel

Sources & evidence

ORD record
ord-76ab63cba5e147ad89ae61ca68ae89d3
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Reaction notes

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