Acetic Acid → HCID 18470752, compound

HRID 2228623Notes

Reaction equation

HRID 2228623 reaction equation
O[N:2]=[C:3]([C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1)[C:4](=O)[CH3:5].[CH3:13][CH:14]1[CH2:19][C:18](=[O:20])[CH2:17][C:16](=O)[CH2:15]1.C(O)(=O)C.[OH-].[Na+]>[Zn].CCOC(C)=O.O>[CH3:5][C:4]1[C:17]2[C:18](=[O:20])[CH2:19][CH:14]([CH3:13])[CH2:15][C:16]=2[NH:2][C:3]=1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 4580955-Methylcyclohexane-1,3-dioneHCID 136352423HCID 136352423, compound

Product 1

HCID 18470752HCID 18470752, compoundYield 17%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

According to the literature procedure (Chiswell, B. Inorganica Chimica Acta. 1972, 629), a mixture of 1-hydroxyimino-1-(4-pyridyl)-2-propanone (Tanaka, A et. al., Chem. Pharm. Bull., 1992, 40, 3206) (0.49 g, 3.0 mmol), 5-methyl-1,3-cyclohexanedione (0.38 g, 3.0 mmol), glacial acetic acid (2.4 mL) and H2O (0.6 mL) was stirred vigorously at room temperature. To this flask, zinc dust (0.6 g) was added slowly keeping the temperature below 60° C. Afer addition, the resulting brown solution was heated under reflux condition for 2 hours. After cooling down to room temperature, the reaction mixture was basified by an addition of 2 M aqueous NaOH, then filtered. The filtrate was extracted with CH2Cl2 (20 mL×3), the combined organic layer was dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography (1-5:1 EtOAc-Hexane then EtOAc only) to give the desired product (0.12 g, 17% yield).

Workup

  1. customthe temperature below 60° C
  2. additionAfer addition
  3. temperaturethe resulting brown solution was heated
  4. temperatureunder reflux condition for 2 hours
  5. filtrationfiltered
  6. extractionThe filtrate was extracted with CH2Cl2 (20 mL×3)
  7. dry with materialthe combined organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash chromatography (1-5:1 EtOAc-Hexane

Sources & evidence

ORD record
ord-2db6647bc0634c0294681545871cd5fd
Source dataset
uspto-grants-2002_07
Patent number
US06417202B1

Reaction notes

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