7-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one → 7-Amino-1,2,4,5-tetrahydro-(2,4)-benzodiazepin-3-one

HRID 1687033Notes

Reaction equation

HRID 1687033 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][NH:9][C:10](=[O:13])[NH:11][CH2:12][C:6]=2[CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[CH:15]=[CH:14][C:7]2[CH2:8][NH:9][C:10](=[O:13])[NH:11][CH2:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 105125087-Nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-oneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 578538687-Amino-1,2,4,5-tetrahydro-(2,4)-benzodiazepin-3-oneYield 70.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 7-nitro-1,2,4,5-tetrahydro-benzo(e)(1,3)diazepin-3-one (2.00 g, 9.65 mmol) was dissolved in methanol (60 mL) and the solution was carefully added to a Parr shaker vessel containing 10% Palladium/Carbon (200 mg) under nitrogen. The reaction was then shaken under 50 psi of hydrogen until uptake of hydrogen had ceased (3 hours). Catalyst was then removed via filtration through a Celite pad. The filter cake was rinsed with methanol (3×50 mL) and the filtrate was reduced en vacuo to afford 1.20 g of 7-amino-1,2,4,5-tetrahydro-(2,4)-benzodiazepin-3-one as a white solid. LC/MS (ESI)=178.32 (M+H). Rf: (10% MeOH/DCM)=0.31.

Workup

  1. additionthe solution was carefully added to a Parr shaker vessel
  2. custom(3 hours)
  3. customCatalyst was then removed via filtration through a Celite pad
  4. washThe filter cake was rinsed with methanol (3×50 mL)

Sources & evidence

ORD record
ord-220d03f07ae1497396c1b8193e5350b3
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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