3-Fluoro-4-hydroxybenzohydrazide → 3-Fluoro-4-hydroxybenzoic Acid {4-[2-(1,2,3,4-Tetrahydro-isoquinolin-2-yl)ethoxy]-2-methoxybenzylidene}hydrazide

HRID 1166783Notes

Reaction equation

HRID 1166783 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[OH:12])[C:5]([NH:7][NH2:8])=[O:6].[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[C:28]([O:34][CH3:35])[CH:27]=1>>[CH2:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][CH2:15][N:14]1[CH2:23][CH2:24][O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[N:8][NH:7][C:5](=[O:6])[C:4]2[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([F:1])[CH:3]=2)=[C:28]([O:34][CH3:35])[CH:27]=1

Participants

3

Reactant 2

HCID 109099793-Fluoro-4-hydroxybenzohydrazideHCID 229991434-[2-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethoxy]-2-methoxybenzaldehyde

Product 1

HCID 725143473-Fluoro-4-hydroxybenzoic Acid {4-[2-(1,2,3,4-Tetrahydro-isoquinolin-2-yl)ethoxy]-2-methoxybenzylidene}hydrazideYield 29.8%

Procedure

This compound was prepared similarly as described in the previous example starting from resin bound 3-fluoro-4-hydroxybenzoic acid hydrazide (1 g, 0.94 mmol) and the above 4-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethoxy]-2-methoxybenzaldehyde (0.4 g, 0.94 mmol). After cleavage the compound was purified by column chromatography to afford 0.13 g of the title compound.

Workup

  1. customThis compound was prepared similarly
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-c041553ef04e4bb9a0ac8bfac3a6d348
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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