HCID 58307233, compound → HCID 58307344, compound

HRID 448374Notes

Reaction equation

HRID 448374 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:15]=1[N+:16]([O-])=O)[O:6][CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH3:11].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:12][N:10]([CH3:11])[CH2:9][CH2:8][CH2:7][O:6][C:5]1[CH:13]=[CH:14][C:15]([NH2:16])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 2

HCID 58307233HCID 58307233, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58307344HCID 58307344, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [3-(3-methoxy-4-nitrophenoxy)propyl]dimethylamine (2.0 g, 7.7 mmol) and 5% Pd—C (0.4 g) in ethyl acetate (75 mL) was shaken under 50 psi of hydrogen for 24 hours. The mixture was filtered through Celite and evaporated, providing 1.7 g of the product as a light grey oil, in 97% yield: 1H NMR (CDCl3) δ 1.86-1.98 (m, 2H), 2.25 (s, 6H), 2.44 (t, J=7.3 Hz, 2H), 3.44 (br, 2H), 3.82 (s, 3H), 3.94 (t, J=6.5 Hz, 2H), 6.35 (dd, J=8.4 Hz, J=2.6 Hz, 1H), 6.46 (d, J=2.6 Hz, 1H), 6.62 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-9bf212d357064ac49b5d334f4d7ebb92
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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