Lithium Hydroxide → HCID 18412671, compound

HRID 50192Notes

Reaction equation

HRID 50192 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([O-:13])=[O:12])[CH:10]=[C:5]2[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=1.[OH-].[Li+]>CO.O>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=[O:12])[CH:10]=[C:5]2[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[N:23])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18412676HCID 18412676, compound

Product 1

HCID 18412671HCID 18412671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3.2 g (10 mmol) of 3-methyl-2-[2-(4-cyanophenyl)ethyl]imidazo[4,5-b]pyridine-6-carboxylate in 150 mL methanol was mixed with a solution of 1.5 g lithium hydroxide in 20 mL water and stirred for 24 hours at room temperature. Then the mixture was diluted with 50 mL of water, the alcohol was distilled off and the aqueous phase was washed with ethyl acetate. After acidification with dilute hydrochloric acid, the mixture was extracted several times with dichloromethane/methanol (9:1), the organic phase was dried with sodium sulfate and the solvent was distilled off. Yield: 2.1 g beige solid (70% of theory); Rf value: 0.38 (silica gel; ethyl acetate/ethanol/ammonia=50:45:5).

Workup

  1. distillationthe alcohol was distilled off
  2. washthe aqueous phase was washed with ethyl acetate
  3. extractionAfter acidification with dilute hydrochloric acid, the mixture was extracted several times with dichloromethane/methanol (9:1)
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-43a1f8226f594ab5a2713a6c34f260ab
Source dataset
uspto-grants-2004_03
Patent number
US06710055B2

Reaction notes

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