HCID 22405127, compound → HCID 22405050, compound

HRID 441237Notes

Reaction equation

HRID 441237 reaction equation
[N+:1]([C:4]1[CH:33]=[CH:32][C:7]([C:8]([N:10]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]([C:21](=[O:31])[C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][CH:23]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O>C(O)C.C(O)(=O)C.[Fe]>[NH2:28][C:25]1[CH:24]=[CH:23][C:22]([C:21]([N:14]2[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[N:10]([C:8](=[O:9])[C:7]3[CH:32]=[CH:33][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:11][CH2:12][CH2:13]2)=[O:31])=[CH:27][CH:26]=1

Participants

5

Reactant 1

HCID 22405127HCID 22405127, compound

Product 1

HCID 22405050HCID 22405050, compound

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 1,5-bis(4-nitrobenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (737 mg) and iron powder (738 mg) in a mixture of ethanol (10 ml) and acetic acid (1 ml) was refluxed for 2 hours and the solution was cooled to ambient temperature. The mixture was filtered through a bed of celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform and the solution was basified with saturated aqueous sodium bicarbonate solution. The solution was filtered through a bed of celite, and then the filtrate was washed with brine. Drying, filtering and the removal of solvents afforded a crude product. The crude product was chromatographed on silica gel (eluent: 2% methanol in chloroform) to give 1,5-bis(4-aminobenzoyl)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine as a slightly yellow powder.

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationThe mixture was filtered through a bed of celite
  3. customthe filtrate was evaporated in vacuo
  4. dissolutionThe residue was dissolved in chloroform
  5. filtrationThe solution was filtered through a bed of celite
  6. washthe filtrate was washed with brine
  7. customDrying
  8. filtrationfiltering
  9. customthe removal of solvents
  10. customafforded a crude product
  11. customThe crude product was chromatographed on silica gel (eluent: 2% methanol in chloroform)

Sources & evidence

ORD record
ord-419ace0f02894da0ad9999f527ab278c
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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