Methanol → HCID 68975129, compound

HRID 540851Notes

Reaction equation

HRID 540851 reaction equation
[CH3:1][N:2]1[C:14]2[C:13]3[CH:12]=[C:11]([O:15][CH2:16][C:17]([O:19]CC)=[O:18])[CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:22].[OH-].[K+].CO>O>[CH3:1][N:2]1[C:14]2[C:13]3[CH:12]=[C:11]([O:15][CH2:16][C:17]([OH:19])=[O:18])[CH:10]=[CH:9][C:8]=3[N:7]=[CH:6][C:5]=2[N:4]=[C:3]1[CH3:22]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68968504HCID 68968504, compound

Product 1

HCID 68975129HCID 68975129, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 2-[(1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]acetate (1.6 g, 5.35 mmol) was added to a solution of potassium hydroxide (0.90 g, 0.16 mol) in a 50:50 mixture of methanol:water (30 mL). The solution was stirred under a nitrogen atmosphere until it was complete as evidenced by HPLC analysis. The methanol was removed under reduced pressure, and 6 N aqueous hydrochloric acid was added until the solution exhibited a neutral pH. A precipitate formed and was isolated by filtration to provide 1.25 g of 2-[(1,2-dimethyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]acetic acid as a white solid, mp 290° C. (decomposition).

Workup

  1. customThe methanol was removed under reduced pressure, and 6 N aqueous hydrochloric acid
  2. additionwas added until the solution
  3. customA precipitate formed
  4. customwas isolated by filtration

Sources & evidence

ORD record
ord-1343eab12e2943e68093811c9a1140ff
Source dataset
uspto-grants-2014_10
Patent number
US08871782B2

Reaction notes

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