Benzyl Bromide → HCID 12111719, compound

HRID 2308134Notes

Reaction equation

HRID 2308134 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:13]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH:5]=[O:6])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 697123-Hydroxy-4-nitrobenzaldehyde

Product 1

HCID 12111719HCID 12111719, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In this synthesis the new (4-amino or substituted amino-3-hydroxyphenyl)-alkylnitriles of Formula (1), of this invention, where R2 is H, can be prepared by reaction of a 3-hydroxy-4-nitrobenzaldehyde of Formula (2) with a benzyl halide, such as benzyl bromide, in the presence of an inorganic base such as potassium carbonate in dimethylformamide (DMF) at room temperature for about 18 hours to produce the 3-benzyloxy-4-nitro-benzaldehyde compound of Formula (3) in about 98% yield; then reacting the compound of Formula (3) with diethyl cyanoalkylphosphonate of Formula (4) in a suspension of sodium hydride in anhydrous THF at room temperature for about 2 hours to produce 3-(3-benzyloxy-4-nitro-phenyl)-acrylonitrile of Formula (5) in about 100% yield; catalytically hydrogenating the compound of Formula (5) with 10% Pd on carbon at about 60 psi hydrogen at room temperature for about 4 hours to provide a compound of Formula (1) where R2 is H in about 100% yield.

Sources & evidence

ORD record
ord-c8e5e9ac58be4c1383344a3c283d1048
Source dataset
uspto-grants-2004_12
Patent number
US06835213B2

Reaction notes

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