HCID 54348404, compound → 4-[2-(3,4,5-trimethoxyphenyl)ethyl]aniline

HRID 488494Notes

Reaction equation

HRID 488494 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=2)[CH:6]=[C:5]([O:20][CH3:21])[C:4]=1[O:22][CH3:23]>C1COCC1.[Ni]>[CH3:21][O:20][C:5]1[CH:6]=[C:7]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:22][CH3:23]

Participants

4

Reactant 1

HCID 54348404HCID 54348404, compound

Product 1

HCID 3647054-[2-(3,4,5-trimethoxyphenyl)ethyl]anilineYield 76.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 1,2,3-trimethoxy-5-[2-(4-nitrophenyl)ethenyl]benzene (9.5 g, 0.03 mol) and Ra—Ni (1.0 g) in THF (50 mL) at 21-26° C. (ΔP=9.6 psi) under a hydrogen atmosphere using the procedure described in Example 1, Step B. This procedure yielded a tan powder, 6.6 g (0.023 mol, 74%) of the desired product. mp 91-93° C.

Sources & evidence

ORD record
ord-e3055b91efbc4720ba401084e3116520
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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