Lithium Hydroxide → HCID 18412671, compound

HRID 2288322Notes

Reaction equation

HRID 2288322 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([O:13]C)=[O:12])[CH:10]=[C:5]2[N:4]=[C:3]1[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=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[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]#[N:24])=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18412708HCID 18412708, compound

Product 1

HCID 18412671HCID 18412671, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A solution of 3.2 g (10 mMol) of methyl 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 sulphate 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 sulphate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-b63c5967401d4c65b256f5da56ed1d9d
Source dataset
uspto-grants-2000_07
Patent number
US06087380

Reaction notes

Loading…