[2-(3-Isopropoxy-4-nitrophenoxy)ethyl]dimethylamine → 4-(2-Dimethylaminoethoxy)-2-isopropoxyphenylamine

HRID 448381Notes

Reaction equation

HRID 448381 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[O:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:12][N:11]([CH3:13])[CH2:10][CH2:9][O:8][C:7]1[CH:14]=[CH:15][C:16]([NH2:17])=[C:5]([O:4][CH:1]([CH3:2])[CH3:3])[CH:6]=1

Participants

5

Reactant 2

HCID 58307279[2-(3-Isopropoxy-4-nitrophenoxy)ethyl]dimethylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 583071884-(2-Dimethylaminoethoxy)-2-isopropoxyphenylamineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of [2-(3-isopropoxy-4-nitrophenoxy)ethyl]dimethylamine (2.0 g, 7.5 mmol) and 5% Pd—C (0.3 g) in ethyl acetate (70 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 gold oil, in 98% yield; 1H NMR (CDCl3) δ 1.34 (d, J=6.0 Hz, 6H), 2.32 (s, 6H), 2.68 (t, J=5.8 Hz, 2H), 3.48 (br, 2H), 3.98 (t, J=5.8 Hz, 2H), 4.48 (septet, J=6.0 Hz, 1H), 6.35 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.50 (d, J=2.5 Hz, 1H), 6.63 (d, J=8.4 Hz, 1H).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated

Sources & evidence

ORD record
ord-b6e6b51d5a874d1a8b6614c95d0668a4
Source dataset
uspto-grants-2013_07
Patent number
US08481568B2

Reaction notes

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