Hydroxyamine hydrochloride → 3-(3,3-Dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde Oxime

HRID 1690735Notes

Reaction equation

HRID 1690735 reaction equation
[CH3:1][C:2]1([CH3:20])[CH:11]([N:12]2[C:16]([CH:17]=O)=[CH:15][N:14]=[CH:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:19])[O:3]1.C([O-])(O)=O.[Na+].Cl.[NH2:27][OH:28]>C(O)C.O>[CH3:1][C:2]1([CH3:20])[CH:11]([N:12]2[C:16]([CH:17]=[N:27][OH:28])=[CH:15][N:14]=[CH:13]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:19])[O:3]1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 248026903-(3,3-dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde

Product 1

HCID 743201913-(3,3-Dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde Oxime

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

3-(3,3-Dimethyl-1-oxo-isochroman-4-yl)-3H-imidazole-4-carbaldehyde (0.100 g, 0.363 mmol) (Example 9a) in ethanol (3 mL) is added to NaHCO3 (0.246 g, 2.901 mmol) and hydroxylamine hydrochloride (0.208 g, 2.901 mmol) in water (1 mL). After 1 hr, water is added and the mixture is extracted three times with dichloromethane. The combined organic phase is dried over magnesium sulfate and filtered through a cotton plug. Concentration in vacuo gives a residue, which is purified by silica gel flash chromatography (elution with dichloromethane-methanol, 49:1), resulting in the separation of the two isomers. Each isomer is obtained as a white solid.

Workup

  1. extractionthe mixture is extracted three times with dichloromethane
  2. dry with materialThe combined organic phase is dried over magnesium sulfate
  3. filtrationfiltered through a cotton plug
  4. concentrationConcentration in vacuo
  5. customgives a residue, which
  6. customis purified by silica gel flash chromatography (elution with dichloromethane-methanol, 49:1)
  7. customresulting in the separation of the two isomers
  8. customEach isomer is obtained as a white solid

Sources & evidence

ORD record
ord-9402923eddc34e4384a48897a368ee88
Source dataset
uspto-grants-2012_04
Patent number
US08153674B2

Reaction notes

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