Ethanol → HCID 67264542, compound

HRID 1687360Notes

Reaction equation

HRID 1687360 reaction equation
[CH2:1]([N:3]1[C:9]2[CH:10]=[C:11]([N+:16]([O-])=O)[C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][N:6]([CH2:19][CH3:20])[CH2:5][C:4]1=[O:21])[CH3:2].C(O)C.C(OCC)(=O)C>[Pd]>[NH2:16][C:11]1[C:12]([O:14][CH3:15])=[CH:13][C:8]2[CH2:7][N:6]([CH2:19][CH3:20])[CH2:5][C:4](=[O:21])[N:3]([CH2:1][CH3:2])[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8857Ethyl AcetateHCID 67264320HCID 67264320, compound

Product 1

HCID 67264542HCID 67264542, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1,4-Diethyl-7-methoxy-8-nitro-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one (0.50 g, 0.0017 mol) was hydrogenated in a solution of Ethanol (40 mL, 0.7 mol), Ethyl acetate (40 mL, 0.4 mol) and 10% Pd/C (10:90, Palladium:carbon black, 0.05 g) for 12 hrs. The reaction was filtered and the filtrate evaporated to give an oil. This was chromatographed on Alumina (12 g) and eluded with DCM/EtOH (20-1) to give 8-Amino-1,4-diethyl-7-methoxy-1,3,4,5-tetrahydro-benzo[e][1,4]diazepin-2-one as an oil (0.33 g, 74%). LCMS (m/e) 264 (M+1); 1H-NMR (DMSO, 400 MHz) δ 6.76 (s, 1H), 6.61 (s, 1H), 5.75 (s, 1H), 4.86 (s, 2H), 3.77 (s, 3H), 3.72-70 (q, 2H, J=6.06 Hz), 3.38 (s, 2H), 2.89 (s, 2H), 1.05-01 (t, 3H, J=7.07 Hz).

Workup

  1. filtrationThe reaction was filtered
  2. customthe filtrate evaporated
  3. customto give an oil
  4. customThis was chromatographed on Alumina (12 g)

Sources & evidence

ORD record
ord-79f880557b54425fa2dcea571eb1a46e
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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