Hydroxyamine hydrochloride → 5-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde-oxime

HRID 1720330Notes

Reaction equation

HRID 1720330 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:22][O:23][CH3:24])=[C:11]([CH:20]=O)[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:4][CH:3]=1.Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:8]=2[C:9]2[C:10]([CH2:22][O:23][CH3:24])=[C:11]([CH:20]=[N:28][OH:29])[N:12]=[CH:13][C:14]=2[NH:15]3)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 224177275-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde

Product 1

HCID 1363755785-(4-Chlorobenzyl)-4-methoxymethyl-beta-carboline-3-carbaldehyde-oximeYield 63.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

0.75 g (0.002 mol) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carbaldehyde is heated one hour to 105° C. with 0.18 g (0.0026 mol) of hydroxylaminehydrochloride in 19 ml of pyridine. 0.48 g (61% of theory) of 5-(4-chlorobenzyl)-4-methoxymethyl-β-carboline-3-carbaldehyde-oxime is obtained from the evaporation residue after recrystallization from ethanol, melting point 224°-228° C.

Sources & evidence

ORD record
ord-4ef82d3220e143a983f691406fb0071d
Source dataset
uspto-grants-1996_04
Patent number
US05506234

Reaction notes

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