6-Nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one → 6-Amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

HRID 1040689Notes

Reaction equation

HRID 1040689 reaction equation
[N+:1]([C:4]1[C:14]2[C:13](=[O:15])[NH:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[NH2:1][C:4]1[C:14]2[C:13](=[O:15])[NH:12][CH2:11][CH2:10][NH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 578538616-Nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 672647516-Amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 6-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (0.2 g, 0.0011 mols) in methanol (8 mL) in a Parr bottle was added 10% palladium on carbon and the mixture subjected to hydrogen at 50 psi for 4 h. The reaction mixture was filtered through celite and washed with DMF and methanol. The filtrate was concentrated in vacuo to give 6-amino-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one and carried on without purification. 1H NMR (400 MHz, DMSO-d6) δ 9.61 (s, 1H), 6.87 (d, 1H, J=7.6 Hz), 6.75-6.88 (m, 2H), 3.59 (t, 2H, J=6 Hz), 2.46 (t, 2H, J=6 Hz); MS (m/e) 178 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with DMF and methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c95d45fe7a31457490e847c2564633b2
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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