Nitromethane → 2-(2,6-Dimethoxyphenyl)ethanamine

HRID 861585

Reaction equation

HRID 861585 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=O.[N+:13]([CH3:16])([O-:15])=[O:14]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH2:5][CH2:16][NH2:13].[CH3:1][O:2][C:3]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:4]=1[CH:5]=[CH:16][N+:13]([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 6375NitromethaneHCID 964042,6-Dimethoxybenzaldehyde

Product 2

HCID 4176022-(2,6-Dimethoxyphenyl)ethanamineHCID 538997621,3-Dimethoxy-2-(2-nitroethen-1-yl)benzene

Procedure

The starting material 2,6-dimethoxy-phenethylamine was prepared from 2,6-dimethoxy-benzaldehyde. Reaction with nitromethane according to the procedure described in Vogel, Textbook of Practical Organic Chemistry, p. 176 (Longman 1978, 4th Ed.) yielded 2,6-dimethoxy-β-nitrostyrene. This compound (1.1 g, 5.3 mmole) was dissolved in diethyl ether/tetrahydrofuran (2:1, 200 ml) and lithium aluminium hydride (0.5 g, 13 mmol) was added in small portions. The mixture was refluxed for 120 minutes and then treated with 0.6 ml H2O, 0.6 ml 15% NaOH (aq) and 1.8 ml H2O. The mixture was filtered and purified by acid-base partitioning (NH4OH (aq) HCl dil. (aq)) and evaporated. The crude product 2,6-dimethoxyphenethylamine was pure enough to be used directly in the following reaction where it was condensed with the product of Example 103, in a manner analogous to Example 105, to give the titled product.

Sources & evidence

ORD record
ord-103d0de9765542debecca06f72996cfb
Source dataset
uspto-grants-1998_02
Patent number
US05714503

Linked notes

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