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

HRID 1687196Notes

Reaction equation

HRID 1687196 reaction equation
O.NN.[N+:4]([C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[O:17])[C:11]=2[CH:18]=1)([O-])=O>[Pd].C(O)C>[NH2:4][C:7]1[CH:8]=[CH:9][C:10]2[CH2:16][CH2:15][CH2:14][NH:13][C:12](=[O:17])[C:11]=2[CH:18]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 588212698-Nitro-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one

Product 1

HCID 672647208-amino-2,3,4,5-tetrahydro-1H-2-benzazepin-1-oneYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Added 65 mL of ethanol, 10% Palladium on activated carbon (50% wet with water for safety) (513 mg), and hydrazine monohydrate (965 ul) to 8-Nitro-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (1.024 g, 4.966 mmol). Heated reaction to 60° C. for 16 hours. Filtered reaction through Celite, and concentrated under reduced pressure. Purified with normal phase silica gel chromatography to obtain a white solid, 8-Amino-2,3,4,5-tetrahydro-benzo[c]azepin-1-one (799 mg, 91%). LCMS: m/z=177.03 (M+H+), 1H NMR (400 MHz, CD3OD) δ 7.00 (d, 1H, J=8.1 Hz), 6.96 (m, 1H), 6.80 (m, 1H), 3.33 (m, 3H), 3.06 (m, 2H), 2.71 (m, 2H), 1.96 (m, 2H).

Workup

  1. temperatureHeated
  2. customreaction to 60° C. for 16 hours
  3. filtrationFiltered
  4. customreaction through Celite
  5. concentrationconcentrated under reduced pressure
  6. customPurified with normal phase silica gel chromatography

Sources & evidence

ORD record
ord-015379631a4342848ce7e4197a299b78
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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