Ethanol → HCID 67263521, compound

HRID 1041481Notes

Reaction equation

HRID 1041481 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[C:7](=[O:19])[N:6]([CH2:20][CH3:21])[CH2:5][CH2:4]1)[CH3:2].C(O)C>[Pd]>[NH2:16][C:11]1[C:12]([O:14][CH3:15])=[CH:13][C:8]2[C:7](=[O:19])[N:6]([CH2:20][CH3:21])[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[C:9]=2[CH:10]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 67263709HCID 67263709, compound

Product 1

HCID 67263521HCID 67263521, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Into a round bottom flask, 1,4-diethyl-7-methoxy-8-nitro-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one (230 mg), 10% Pd/C, (50.0 mg) and ethanol (20 mL, 0.4 mol) were added. The mixture was evacuated and charged with hydrogen (3×). The reaction was stirred under hydrogen balloon for 4 hours. The solid was filtered through Celite. The organic was removed under vacuum to give 8-amino-1,4-diethyl-7-methoxy-1,2,3,4-tetrahydro-benzo[e][1,4]diazepin-5-one as a brown solid (0.21 g, 100%). 1H-NMR (CDCl3, 400 MHz): δ 7.08 (s, 1H), 6.24 (s, 1H), 4.17 (s, 2H), 3.78 (s, 3H), 3.59 (q, 2H), 3.33 (t, 2H), 3.16 (t, 2H), 3.02 (q, 2H), 1.23 (t, 3H), 1.10 (t, 3H).

Workup

  1. customThe mixture was evacuated
  2. additioncharged with hydrogen (3×)
  3. filtrationThe solid was filtered through Celite
  4. customThe organic was removed under vacuum

Sources & evidence

ORD record
ord-68927aa8d68e4e57b15c1a9fcc4bb6c6
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

Loading…