4-Nitrobenzaldehyde → 2-amino-1-(4-nitrophenyl)ethanol

HRID 2053398Notes

Reaction equation

HRID 2053398 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:12]([CH3:15])([O-])=O>>[NH2:12][CH2:15][CH:8]([OH:9])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1

Participants

3

Reactant 2

HCID 5414-NitrobenzaldehydeHCID 6375Nitromethane

Product 1

HCID 28314052-amino-1-(4-nitrophenyl)ethanol

Procedure

The method of Schoenenberger, Archiv. der Pharmazie, 1975, 308(9), 717-719 can be employed. 4-Nitrobenzaldehyde can be reacted with nitromethane and base, followed by selective reduction of the aliphatic nitro group to yield 1-amino-2-hydroxy-2-(4-nitrophenyl) ethane. This substance can be reacted with 2,6-dichlorobenzaldehyde to yield a mixture of cis-(±) and trans-(±)-2-(2,6-dichlorophenyl)-5-(4-nitrophenyl)-1,3-oxazolidines. The nitrophenyl group can be reduced with tin (II) dichloride or iron powder and ammonium chloride to yield the corresponding aniline. This aniline can be reacted with 2,2-dichloroacetyl chloride and triethylamine to yield a mixture of cis-(±) and trans-(±)-2,2-dichloro-N-[4-[2-(2,6-dichlorophenyl)-5-(1,3-oxazolidinyl)]phenyl]acetamides.

Sources & evidence

ORD record
ord-cbc3b963a79a4e269ba3cafb128e5dba
Source dataset
uspto-grants-2008_02
Patent number
US07326790B2

Reaction notes

Loading…