4-Nitrobenzaldehyde → HCID 21559167, compound

HRID 1578512Notes

Reaction equation

[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:17]([C:20]1[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=1)([O-])=O.[OH-].[K+]>>[CH2:1]([CH:8]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([NH2:17])=[CH:21][CH:22]=2)[C:9]1=[O:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 5414-Nitrobenzaldehyde

HCID 14797Potassium Hydroxide

HCID 30477552-Benzylcyclooctan-1-one

Product 1

HCID 21559167HCID 21559167, compound

Procedure

This example illustrates the preparation of benzylcyclooctanones wherein the aromatic ring is substituted with an amino group. 2-Benzylcyclooctanone is allowed to react with equimolar amounts of p-nitrobenzaldehyde in refluxing methanolic potassium hydroxide for 3 hours. The 2-benzyl-8-(p-nitrobenzylidene)cyclooctanone which forms is removed by filtration and subjected to hydrogenation at 50 p.s.i.g. in the presence of 10 percent palladium on carbon using a solvent system comprising equal portions of ethyl acetate and acetic acid. The 2-benzyl-8-(p-aminobenzyl)cyclooctanone which is obtained from the hydrogenation is purified by converting it to the hydrochloride salt by means of hydrogen chloride introduced into an ethereal solution of the crude product. The melting point of the crude 2-benzyl8-(p-aminobenzyl)cyclooctanone hydrochloride is 175°-195° C.

Workup

customThe 2-benzyl-8-(p-nitrobenzylidene)cyclooctanone which forms is removed by filtration

Sources & evidence

ORD record: ord-2909da98675942979c2b1249f5a17f19
Source dataset: uspto-grants-1976_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03937710

Reaction notes

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