Lithium hydroxide, monohydrate → HCID 68089228, compound

HRID 1772057Notes

Reaction equation

HRID 1772057 reaction equation
[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)[N:4]=[C:3]1[CH:15]([CH3:21])[CH2:16][C:17]([O:19]C)=[O:18].O.[OH-].[Li+]>C(#N)C.O>[CH3:1][N:2]1[C:14]2[C:5](=[C:6]3[C:11](=[CH:12][CH:13]=2)[N:10]=[CH:9][CH:8]=[CH:7]3)[N:4]=[C:3]1[CH:15]([CH3:21])[CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68089342HCID 68089342, compound

Product 1

HCID 68089228HCID 68089228, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 3-(3-methyl-3H-imidazo[4,5-f]quinolin-2-yl)butanoate (560 mg, 1.97 mmol) in acetonitrile (20 mL) and water (8 mL) was added lithium hydroxide hydrate (249 mg, 5.94 mmol). The mixture was stirred at room temperature overnight. The mixture was concentrated to about 8 mL. The pH of the solution was adjusted to ˜4 with 1N HCl aqueous solution. The mixture was concentrated to dryness and to the residue was added 50 mL of DCM/MeOH v/v 10:1. The precipitate was removed by filtration and the filtrate was concentrated to dryness to give the product as a yellow solid (480 mg, 90% yield). ESI MS: m/z 270.1 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated to about 8 mL
  2. concentrationThe mixture was concentrated to dryness and to the residue
  3. additionwas added 50 mL of DCM/MeOH v/v 10:1
  4. customThe precipitate was removed by filtration
  5. concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record
ord-d2b7d74ae0624428a8e1222f0dabbdac
Source dataset
uspto-grants-2016_02
Patent number
US09249162B2

Reaction notes

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