Ethanol → HCID 67264093, compound

HRID 1687817Notes

Reaction equation

HRID 1687817 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:7]=2[NH:6][CH2:5][CH2:4]1)[CH3:2].C(O)C>[Pd]>[NH2:15][C:13]1[CH:12]=[CH:11][C:8]2[C:9](=[O:10])[N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]=2[CH:14]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67263507HCID 67263507, compound

Product 1

HCID 67264093HCID 67264093, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a Round bottom flask, 4-Ethyl-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (3.80 g, 0.0162 mol), Ethanol (100 mL, 2 mol;) and 10% Pd/C (10:90, Palladium:carbon black, 0.50 g) were added. The mixture was evacuated and charged with hydrogen (3 times). The reaction was stirred at room temperature overnight under an atmosphere of Hydrogen via a balloon. The solid was filtered and washed with ethanol. The solvent was removed under vacuum to give 8-amino-4-ethyl-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a white solid. 1H-NMR (DMSO-D6, 400 MHz): δ 7.35 (d, 1H), 5.95 (d, 1H), 5.85 (s, 1H), 5.78 (s, 1H), 5.20 (s, 2H), 3.26-3.50 (m, 6H), 1.08 (t, 3H)

Workup

  1. customThe mixture was evacuated
  2. additioncharged with hydrogen (3 times)
  3. filtrationThe solid was filtered
  4. washwashed with ethanol
  5. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a70a47e63d6940adafeee371e9affc2f
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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