HCID 59452837, compound → HCID 39239230, compound

HRID 419327Notes

Reaction equation

HRID 419327 reaction equation
[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([N+:13]([O-])=O)[CH:7]=1>[Pd].CCO>[CH3:1][N:2]([CH3:16])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([CH:7]=1)[NH2:13]

Participants

4

Reactant 1

HCID 59452837HCID 59452837, compound

Product 1

HCID 39239230HCID 39239230, compoundYield 107.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Palladium on carbon (10% by weight, 300 mg) and N,N-dimethyl-2-[(4-methyl-3-nitrophenyl)oxy]ethanamine (2.6 g, 12 mmol), dissolved in EtOH (40 mL), were transferred to a Fischer-Porter vessel. The vessel was evacuated twice and back-filled with N2. The N2 pressure was released and the vessel kept under a 60 psi of H2 pressure for 12 h. The H2 pressure was released, the reaction filtered through celite, and concentrated to provide the title compound (2.5 g, 95% yield). 1H NMR (400 MHz, CDCl3) δ ppm 2.09 (s, 3H), 2.32 (s, 6H), 2.69 (t, J=5.9 Hz, 2H), 3.58 (br s, 2H), 4.01 (t, J=5.9 Hz, 2H), 6.27-6.31 (m, 2H), 6.90-6.95 (m, 1H).

Workup

  1. customThe vessel was evacuated twice
  2. additionback-filled with N2
  3. filtrationthe reaction filtered through celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-55caae9e15d143039e52f9c407da8321
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

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