Hydrazine hydrate (1:1) → 2H-1-Benzazepin-2-one, 8-amino-1-ethyl-1,3,4,5-tetrahydro-

HRID 1040855Notes

Reaction equation

HRID 1040855 reaction equation
CO[CH2:3][CH2:4][N:5]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[CH2:9][CH2:8][CH2:7][C:6]1=[O:19].O.NN>CCO.[Pd]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:19])[N:5]([CH2:4][CH3:3])[C:11]=2[CH:12]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 672644411-(2-Methoxy-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 113.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-(2-methoxy-ethyl)-8-nitro-1,3,4,5-tetrahydro-1-benzazepin-2-one (1.00 g, 3.9 mmol) in EtOH (13 mL) was sequentially added 10% Pd/C (155 mg) and hydrazine-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 (901 mg, 98%) that had the following properties: LC/MS (ESI+): 235 (M+H); 1H-NMR (CDCl3, 400 MHz): δ 6.95 (d, J=7.9, 1H), 6.68 (s, 1H), 6.51 (d, J=7.9, 1H), 3.95 (br s, 2H), 3.67 (br s, 2H), 3.56 (m, 2H), 3.32 (d, 3H, J=2.2), 2.75 (br s, 2H), 2.30 (m, 2H), 2.10 (m, 2H).

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-c6e275f6a441494986249a2580a75ff4
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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