Nitrobenzene → HCID 53659154, compound

HRID 1979488Notes

Reaction equation

HRID 1979488 reaction equation
[N+](C1C=CC=CC=1)([O-])=O.[O:10]=[C:11]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]([CH:22]2[CH2:27][CH2:26][CH2:25][CH:24]=[CH:23]2)[CH2:13][C@H:12]1[NH:28]C(OCCCC)=O>C1(C)C(C)=CC=CC=1.[C].[Pd]>[O:10]=[C:11]1[NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[N:14]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:13][C@H:12]1[NH2:28]

Participants

5

Reactant 2

HCID 7416NitrobenzeneHCID 57016129HCID 57016129, compound

Product 1

HCID 53659154HCID 53659154, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
50 °C

Procedure

Nitrobenzene (22.16 g) and 10% palladium carbon (6 g) were added to a solution of (3R)-2-oxo-3-butoxycarbonylamino-5-(2-cyclohexen-1-yl)-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (12.87 g) in xylene (200 ml), the mixture was refluxed for one hour and 30 minutes. The reaction mixture was allowed to cool, filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (30 ml), 4N HCl-dioxane (20 ml) was added, the resultant mixture was stirred at 50° C. for one hour. After allowed to cool, crystals so precipitated were collected by filtration, the crystals were washed with 2-propanol, to thereby obtain hydrochloride of the title compound. The compound was dissolved under heating in the mixed solvent of methanol and water, allowed to cool, saturated sodium bicarbonate was added for neutralization, crystals so precipitated were collected be filtration, the crystals were washed with water and dried, to thereby obtain 5.55 g of the title compound (Yield: 86%).

Workup

  1. temperaturethe mixture was refluxed for one hour and 30 minutes
  2. temperatureto cool
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in ethanol (30 ml)
  6. addition4N HCl-dioxane (20 ml) was added
  7. temperatureto cool
  8. customcrystals so precipitated
  9. filtrationwere collected by filtration
  10. washthe crystals were washed with 2-propanol
  11. dissolutionThe compound was dissolved
  12. temperatureunder heating in the mixed solvent of methanol and water
  13. temperatureto cool
  14. additionsaturated sodium bicarbonate was added for neutralization, crystals
  15. customso precipitated
  16. customwere collected
  17. filtrationfiltration
  18. washthe crystals were washed with water
  19. customdried

Sources & evidence

ORD record
ord-9d12eb6255a94347bc6474a5069f0295
Source dataset
uspto-grants-2001_05
Patent number
US06239131B1

Reaction notes

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