Potassium Hydroxide → 5,7-Dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyl indeno[5,6-d]imidazol-6(1H)-one oxime

HRID 979846Notes

Reaction equation

HRID 979846 reaction equation
[OH-:1].[K+].Cl.[NH2:4]O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:20][C:19]3[CH:21]=[C:22]4[C:26](=[CH:27][C:18]=3[N:17]=2)[C:25]([CH3:29])([CH3:28])[C:24](=O)[C:23]4([CH3:32])[CH3:31])[C:9]=1[CH3:33]>CO>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:27]=[C:26]4[C:22](=[CH:21][C:19]=3[N:20]=2)[C:23]([CH3:31])([CH3:32])[C:24](=[N:4][OH:1])[C:25]4([CH3:28])[CH3:29])[C:9]=1[CH3:33]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 98654732-[(4-methoxy-3-methylpyridin-2-yl)methylsulfanyl]-5,5,7,7-tetramethyl-3H-cyclopenta[f]benzimidazol-6-one

Product 1

HCID 740747155,7-Dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyl indeno[5,6-d]imidazol-6(1H)-one oxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 560 mg of potassium hydroxide in 1.4 ml of methanol and a solution of 700 mg of hydroxylamine hydrochloride in 3.6 ml of methanol were mixed together at 40°, whereupon the mixture was stirred for 30 minutes and 300 mg of 5,7-dihydro-2[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethylindeno[5,6-d]imidazol-6(1H)-one were added thereto. The reaction mixture was stirred at 40° under argon for 3 days and then concentrated and treated with methylene chloride/water. The methylene chloride solution was separated, dried, filtered and evaporated. The residue was chromatographed twice on silica gel with methylene chloride/methanol (9:1), the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. 5,7-Dihydro-2-[[(4-methoxy-3-methyl-2-pyridyl)methyl]thio]-5,5,7,7-tetramethyl indeno[5,6-d]imidazol-6(1H)-one oxime was obtained. After recrystallization from ethyl acetate the product melts at 160° with decomposition.

Workup

  1. stirringThe reaction mixture was stirred at 40° under argon for 3 days
  2. concentrationconcentrated
  3. additiontreated with methylene chloride/water
  4. customThe methylene chloride solution was separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed twice on silica gel with methylene chloride/methanol (9:1)
  9. customthe pressure being produced with nitrogen gas

Sources & evidence

ORD record
ord-1be00c50d8144c59a7ec59688845a062
Source dataset
uspto-grants-1987_01
Patent number
US04634710

Reaction notes

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