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 2402549Notes

Reaction equation

HRID 2402549 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].[Pd].C(O)C>[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 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

10% palladium carbon (1.66 g, water content: 54.8%) was added to an ethanol (150 mL) solution of 1-ethyl-7-benzyloxy-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (15.0 g, 42.6 mmol), and catalytic hydrogenation reaction was performed at 40-50° C., at 3 atm. The reaction solution was filtered to remove a catalyst, and ethanol was distilled off. Methanol (105 mL) and water (105 mL) were added to the resulting residue, and the mixture was heated while stirring. After the dissolution was confirmed, stirring under ice cooling was conducted for 1 hour, and precipitated crystals were collected by filtration. The resulting crystals were washed with 50% methanol (30 mL), and dried at 60° C., thereby obtaining 10.7 g of a white, powdery target compound (yield: 96%).

Workup

  1. customwas performed at 40-50° C., at 3 atm
  2. filtrationThe reaction solution was filtered
  3. customto remove a catalyst, and ethanol
  4. distillationwas distilled off
  5. additionMethanol (105 mL) and water (105 mL) were added to the resulting residue
  6. temperaturethe mixture was heated
  7. dissolutionAfter the dissolution
  8. stirringstirring under ice cooling
  9. customprecipitated crystals
  10. filtrationwere collected by filtration
  11. washThe resulting crystals were washed with 50% methanol (30 mL)
  12. customdried at 60° C.

Sources & evidence

ORD record
ord-e4d509fb5af9436c8c04cfcb851daef5
Source dataset
uspto-grants-2014_08
Patent number
US08796447B2

Reaction notes

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