Sodium ethoxide → HCID 68675473, compound

HRID 1183068Notes

Reaction equation

HRID 1183068 reaction equation
[CH2:1]([N:3]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1[N+:20]([O-])=O)[C:4](=[O:11])[CH2:5][C:6](OCC)=[O:7])[CH3:2].[O-]CC.[Na+]>[C].[Pd].C(O)C>[CH2:1]([N:3]1[C:4](=[O:11])[CH2:5][C:6](=[O:7])[NH:20][C:13]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:12]1=2)[CH3:2]

Participants

5

Reactant 2

HCID 2723922Sodium ethoxideHCID 68674369HCID 68674369, compound

Product 1

HCID 68675473HCID 68675473, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Palladium carbon (10%, 1.1 g) was added to an ethanol solution (250 ml) of ethyl N-ethyl-N-(5-methoxy-2-nitrophenyl)malonamate (21.05 g, 67.8 mmol), and cooled in an ice water bath. Catalytic reduction was conducted at about room temperature. Celite filtration was conducted to remove the catalyst, and the filtrate was concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (THF) (200 ml). Sodium ethoxide (6.9 g, 102 mmol) was added thereto, and then heating was conducted under reflux for 15 minutes. The reaction mixture was cooled to room temperature, and the precipitated insoluble matter was collected by filtration. The filtrate was concentrated under reduced pressure. Water was added to the residue and the collected insoluble matter, and the mixture was neutralized with hydrochloric acid. Extraction with ethyl acetate was then performed. The organic layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethanol to thereby obtain 7.9 g (yield: 50%) of 1-ethyl-8-methoxy-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a white powder. The mother liquor was then concentrated, and the residue was purified using a silica gel flash column (n-hexane:ethyl acetate=1:1→0:1) to thereby obtain 2.9 g of object compound.

Workup

  1. temperaturecooled in an ice water bath
  2. customwas conducted at about room temperature
  3. filtrationCelite filtration
  4. customto remove the catalyst
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in tetrahydrofuran (THF) (200 ml)
  7. temperatureheating
  8. temperatureunder reflux for 15 minutes
  9. filtrationthe precipitated insoluble matter was collected by filtration
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. additionWater was added to the residue
  12. extractionExtraction with ethyl acetate
  13. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-cc47d00b88e34c4f8d2ca2e0ac47cfd3
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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