HCID 14256049, compound → 4-[2-(3,4,5-trimethoxyphenyl)ethyl]aniline

HRID 1647294Notes

Reaction equation

HRID 1647294 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([O:22][CH3:23])[C:15]([O:20][CH3:21])=[C:16]([O:18][CH3:19])[CH:17]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 14256049HCID 14256049, compound

Product 1

HCID 3647054-[2-(3,4,5-trimethoxyphenyl)ethyl]anilineYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of nitrostilbene 6l (250 mg, 0.8 mmol) in EtOAc (20 mL) was hydrogenated at 30 psi in the presence of 10% Pd-C (25 mg) at room temperature for 4 h, and the catalyst was filtered off. Evaporation of the solvent and crystallization of the residue from hexanes gave the amine 8z (180 mg, 80%); mp 84°-5° C; IR (KBr) 3450, 3400, 3020, 2920, 2840, 1600, 1580, 1520, 1330, 1240, 1120, 980 cm-1 ; 1H NMR (CDCl3, 300 MHz) d 6.98 (d, J=8.2 Hz, 2H), 6.63 (d, J=8.2 Hz, 2H), 6.63 (d, J=8.2 Hz, 2H), 6.37 (s, 2H), 3.83 (s, 9H), 3.57 (bs, 2H), 2.80 (s, 4H); CIMS (isobutane) m/e 288 (MH+, 100). Anal. (C17H21NO3) C, H.

Workup

  1. filtrationthe catalyst was filtered off
  2. customEvaporation of the solvent and crystallization of the residue from hexanes

Sources & evidence

ORD record
ord-bc41a67373424b5aa70c06b11a0e32a2
Source dataset
uspto-grants-1995_07
Patent number
US05430062

Reaction notes

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