1-Ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione → 1-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 2402550Notes

Reaction equation

HRID 2402550 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([O:19]CC3C=CC=CC=3)[CH:17]=[CH:18][C:4]1=2)[CH3:2]>[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-].CO>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

4

Reactant 1

HCID 509432951-Ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 686733851-Ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 82%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 887MethanolSolvent

Procedure

20% palladium hydroxide carbon (4.00 g) was added to a methanol (400 mL) solution of 1-ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (39.8 g, 113 mmol), and catalytic hydrogenation reaction was performed at room temperature at ordinary pressure. The reaction solution was filtered to remove a catalyst, and methanol was distilled off. Ethanol (120 mL) was added to the resulting residue, and the mixture was heated while stirring. After the dissolution was confirmed, water (40 mL) was added, and the mixture was heated again. After the temperature was cooled to near room temperature, stirring was performed under ice cooling for 1 hour. Precipitated crystals were then collected by filtration. The resulting crystals were washed with 50% ethanol (40 mL), and dried at 60° C., thereby obtaining 24.3 g of white, powdery 1-ethyl-7-hydroxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (yield: 82%).

Workup

  1. customwas performed at room temperature at ordinary pressure
  2. filtrationThe reaction solution was filtered
  3. customto remove a catalyst, and methanol
  4. distillationwas distilled off
  5. additionEthanol (120 mL) was added to the resulting residue
  6. temperaturethe mixture was heated
  7. dissolutionAfter the dissolution
  8. additionwater (40 mL) was added
  9. temperaturethe mixture was heated again
  10. stirringstirring
  11. customPrecipitated crystals
  12. filtrationwere then collected by filtration
  13. washThe resulting crystals were washed with 50% ethanol (40 mL)
  14. customdried at 60° C.

Sources & evidence

ORD record
ord-9ff80d97d83d481891a9ed0a6cf734d1
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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