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

HRID 1687181Notes

Reaction equation

HRID 1687181 reaction equation
C(O)C.O.NN.[CH2:7]([N:9]1[C:15](=[O:16])[CH2:14][CH2:13][C:12]([CH3:18])([CH3:17])[C:11]2[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:10]1=2)[CH3:8]>[Pd].O>[NH2:23][C:20]1[CH:21]=[CH:22][C:10]2[N:9]([CH2:7][CH3:8])[C:15](=[O:16])[CH2:14][CH2:13][C:12]([CH3:17])([CH3:18])[C:11]=2[CH:19]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 67264196HCID 67264196, compound

Product 1

HCID 672637817-Amino-1-ethyl-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-oneYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

Added 30 mL of ethanol, 10% Palladium on activated carbon, 50% wet with water for safety (273 mg), and hydrazine monohydrate (400 ul) to 1-Ethyl-5,5-dimethyl-7-nitro-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (537 mg, 2.047 mmol). Heated reaction to 60° C. for 24 hours. Filtered reaction through Celite, and concentrated under reduced pressure. Purified with normal phase silica gel chromatography eluting with 40% to 60% ethyl acetate in hexane to obtain a yellow sticky solid, 7-Amino-1-ethyl-5,5-dimethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (347 mg, 73%). LCMS: m/z=233.07 (M+H+), 1H NMR (400 MHz, DMSO-d6) δ 6.98 (d, 1H, J=8.9 Hz), 6.59 (d, 1H, J=1.8 Hz), 6.48 (dd, 1H, J=8.3, 1.5 Hz), 5.08 (s, 2H), 3.58 (m, 2H), 1.96 (m, 4H), 1.17 (m, 9H).

Workup

  1. temperatureHeated
  2. customreaction to 60° C. for 24 hours
  3. filtrationFiltered
  4. customreaction through Celite
  5. concentrationconcentrated under reduced pressure
  6. customPurified with normal phase silica gel chromatography
  7. washeluting with 40% to 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1457e4e39a284ab9935c294c505a02b5
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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