Sodium Hydroxide → HCID 9902528, compound

HRID 1417072Notes

Reaction equation

HRID 1417072 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:26])[C:11]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH3:26])[C:11]([C:20]3[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=3)=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15407873HCID 15407873, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9902528HCID 9902528, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-cyanophenyl)-1-methyl-4-phenyl-5-(4-pyridyl)imidazole (0.20 g, 0.6 mmol) [See Ex. 3 above] in THF (10 mL) was added LiAlH4 (0.60 mL of 1.0M solution in THF, 0.6 mmol), and the resulting mixture was stirred at rt for 1 h. The mixture was then poured into 2.5N NaOH and extracted with Et2O. The organic extract was evaporated, and the residue was purified by flash chromatography, eluting first with a solvent gradient of 0-10% MeOH/CHCl3, followed by 1:10:90 NH4OH/MeOH/CHCl3. Trituration with ether afforded the title compound as a white solid (66 mg, 32%): CIMS (NH3, m/z): 341 (M+ +H).

Workup

  1. extractionextracted with Et2O
  2. extractionThe organic extract
  3. customwas evaporated
  4. customthe residue was purified by flash chromatography
  5. washeluting first with a solvent gradient of 0-10% MeOH/CHCl3

Sources & evidence

ORD record
ord-99240887e3c740a1bda8674368359262
Source dataset
uspto-grants-1999_06
Patent number
US05916891

Reaction notes

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