Methanol → 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

HRID 441220Notes

Reaction equation

HRID 441220 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([C:18](=[O:28])[C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)[CH2:10][CH2:9][C:8]1=[O:29])=[O:5])[CH3:2].CO>[Fe].C(O)(=O)C>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:8](=[O:29])[CH2:9][CH2:10]2)=[O:28])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 106684941-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one

Product 1

HCID 104992005-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-oneYield 98.9%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

The mixture of 1-ethoxycarbonylmethyl-5-(4-nitrobenzoyl)-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (667 mg), iron powder (469 mg), methanol (10 ml) and acetic acid (1 ml) was refluxed for 1 hour. The reaction mixture was cooled to ambient temperature and it was filtered through a bed of celite followed by the removal of methanol. The residue was diluted with chloroform and to the mixture was added saturated sodium bicarbonate aqueous solution followed by stirring for 10 minutes. The resulting mixture was filtered through a bed of celite and the organic layer was washed with brine. Drying the filtrate, and the removal of chloroform obtained a crude product. The crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1) to give 5-(4-aminobenzoyl)-1-ethoxycarbonylmethyl-1,3,4,5-tetrahydro-1,5-benzodiazepin-2(2H)-one (610 mg) as a slightly brown powder.

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationit was filtered through a bed of celite
  3. customfollowed by the removal of methanol
  4. additionThe residue was diluted with chloroform and to the mixture
  5. additionwas added saturated sodium bicarbonate aqueous solution
  6. filtrationThe resulting mixture was filtered through a bed of celite
  7. washthe organic layer was washed with brine
  8. customDrying the filtrate
  9. customthe removal of chloroform
  10. customobtained a crude product
  11. customThe crude product was triturated with a mixture of diisopropyl ether and n-hexane (1:1)

Sources & evidence

ORD record
ord-963f6592c1d4418eb6492f2dc72f6b6e
Source dataset
uspto-grants-1996_05
Patent number
US05521170

Reaction notes

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