HCID 58307334, compound → HCID 58307289, compound

HRID 448390Notes

Reaction equation

HRID 448390 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1.[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1

Participants

5

Reactant 2

HCID 58307334HCID 58307334, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58307289HCID 58307289, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture dimethyl-[2-(4-nitro-3-phenoxy-phenoxy)-ethyl]-amine (3.0 g, 9.9 mmol) and 5% Pd—C (0.6 g) in ethyl acetate (100 mL) was shaken under 50 psi of hydrogen for 20 hours. The mixture was filtered through Celite and evaporated, providing 2.7 g of the product, in quantitative yield; 1H NMR (CDCl3) δ 2.30 (s, 6H), 2.65 (t, J=5.7 Hz, 2H), 3.93 (t, J=5.7 Hz, 2H), 6.51 (d, J=2.6 Hz, 1H), 6.60 (dd, J=8.6 Hz, J=2.9 Hz, 1H), 6.74 (d, J=8.6 Hz, 1H), 6.95-7.00 (m, 2H), 7.06 (t, J=7.3 Hz, 1H), 7.28-7.34 (m, 2H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-0ce39bbe6bcf432fb992d016086d163d
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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