1-Ethyl-8-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one → 2H-1-Benzazepin-2-one, 8-amino-1-ethyl-1,3,4,5-tetrahydro-

HRID 1040849Notes

Reaction equation

HRID 1040849 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[CH2:8][CH2:7][CH2:6][C:5]2[CH:11]=[CH:12][C:13]([N+:15]([O-])=O)=[CH:14][C:4]1=2)[CH3:2]>CCO.[Pd]>[NH2:15][C:13]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][C:9](=[O:10])[N:3]([CH2:1][CH3:2])[C:4]=2[CH:14]=1

Participants

4

Reactant 1

HCID 98345831-Ethyl-8-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

Product 1

HCID 98991662H-1-Benzazepin-2-one, 8-amino-1-ethyl-1,3,4,5-tetrahydro-Yield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-ethyl-8-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (920 mg, 3.9 mmol, WO2002100327A2) in EtOH (13 mL) was sequentially added 10% Pd/C (155 mg) and hyrdrazine-monohydrate (3 mL). The solution was warmed to reflux for 2.5 h, cooled, filtered through celite, and repeatedly evaporated from toluene to remove residual hydrazine to afford 8-amino-1-ethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (805 mg, 100%) that had the following properties: LC/MS (ESI+): 205 (M+H); 1H-NMR (CDCl3, 400 MHz): δ 6.97 (d, J=7.8, 1H), 6.55 (s, 1H), 6.52 (d, J=7.8, 1H), 3.95 (br s, 2H), 3.67 (br s, 2H), 2.60 (br s, 2H), 2.29 (m, 2H), 2.11 (m, 2H), 1.15 (t, J=6.2, 3H).

Workup

  1. temperatureThe solution was warmed
  2. temperatureto reflux for 2.5 h
  3. temperaturecooled
  4. filtrationfiltered through celite
  5. customrepeatedly evaporated from toluene
  6. customto remove residual hydrazine

Sources & evidence

ORD record
ord-dc7ec6fb35ea4878b08e190d58d83555
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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