Sodium Hydroxide → HCID 69506840, compound

HRID 2366736Notes

Reaction equation

HRID 2366736 reaction equation
[OH-].[Na+].[CH2:3]([C:6]1[N:7]([CH2:19][C:20]2([C:24]([O:26]CC)=[O:25])[CH2:23][CH2:22][CH2:21]2)[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5]>C(O)C>[CH2:3]([C:6]1[N:7]([CH2:19][C:20]2([C:24]([OH:26])=[O:25])[CH2:23][CH2:22][CH2:21]2)[C:8]2[C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=[CH:10][C:9]=2[N:18]=1)[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57515607HCID 57515607, compound

Product 1

HCID 69506840HCID 69506840, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Aqueous sodium hydroxide (7 mL of 6 M) was added to a solution of ethyl 1-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanecarboxylate (7.55 g, 21.5 mmol) in ethanol (60 mL); the reaction was stirred at ambient temperature for one hour and concentrated under reduced pressure. The residue was dissolved in water (40 mL) and adjusted to pH 7 with the addition of 2 M hydrochloric acid. A precipitate formed, was isolated by filtration, and dried in a vacuum oven at 70° C. for two hours to provide 6.76 g of 1-[(2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]cyclobutanecarboxylic acid as a tan solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water (40 mL)
  3. additionadjusted to pH 7 with the addition of 2 M hydrochloric acid
  4. customA precipitate formed
  5. customwas isolated by filtration
  6. customdried in a vacuum oven at 70° C. for two hours

Sources & evidence

ORD record
ord-9e8327d581d9472c9553f37fd3660eee
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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