Ethanol → 7-Amino-1,5,5-trimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

HRID 1687177Notes

Reaction equation

HRID 1687177 reaction equation
C(O)C.O.NN.[CH3:7][N:8]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]([CH3:17])([CH3:16])[C:10]2[CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=[CH:21][C:9]1=2>[Pd].O>[NH2:22][C:19]1[CH:20]=[CH:21][C:9]2[N:8]([CH3:7])[C:14](=[O:15])[CH2:13][CH2:12][C:11]([CH3:17])([CH3:16])[C:10]=2[CH:18]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 19760205HCID 19760205, compound

Product 1

HCID 197602147-Amino-1,5,5-trimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Added 16 mL of ethanol, 10% Palladium on activated carbon, 50% wet with water for safety (129 mg), and hydrazine monohydrate (200 ul) to 1,5,5-Trimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (257 mg, 1.035 mmol). Heated reaction to 60° C. overnight. Filtered reaction through Celite, and concentrated under reduced pressure to obtain a colorless sticky solid, 7-Amino-1,5,5-trimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (223 mg, 99%). LCMS: m/z=219.04 (M+H+), 1H NMR (400 MHz, DMSO-d6) δ 6.95 (d, 1H, J=8.3 Hz), 6.57 (d, 1H, J=1.5 Hz), 6.48 (dd, 1H, J=8.3, 1.3 Hz), 5.09 (s, 2H), 3.07 (s, 3H), 2.09 (m, 2H), 1.88 (m, 2H), 1.19 (s, 6H).

Workup

  1. temperatureHeated
  2. customreaction to 60° C. overnight
  3. filtrationFiltered
  4. customreaction through Celite
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e7e95b9867c1495aacff83be07418487
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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