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

HRID 1166775Notes

Reaction equation

HRID 1166775 reaction equation
[NH2:1][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>CC(O)C>[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]([NH2:1])[CH:3]=2)=[C:28]([O:34][CH3:35])[CH:27]=1

Participants

4

Reactant 2

HCID 5858793-Amino-4-hydroxybenzohydrazideHCID 229991434-[2-(1,2,3,4-Tetrahydroisoquinolin-2-yl)ethoxy]-2-methoxybenzaldehyde

Product 1

HCID 725145883-Amino-4-hydroxybenzoic Acid {4-[2-(1,2,3,4-Tetrahydro-isoquinolin-2-yl)ethoxy]-2-methoxybenzylidene}hydrazideYield 48%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The above 3-amino-4-hydroxybenzoic acid hydrazide (50 mg, 0.3 mmol) and the above 4-[2-(1,2,3,4-tetrahydroisoquinolin-2-yl)ethoxy]-2-methoxybenzaldehyde (93 mg, 0.3 mmol) were dissolved in 2-propanol (4 ml) and the mixture was heated at reflux temperature for 16 hours. The cooled mixture was filtered and the precipitate was washed with 2-propanol (2×4 ml) and dried by suction to afford 66 mg (48%) of the title compound as a solid. M.p.: 162-164° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 16 hours
  3. filtrationThe cooled mixture was filtered
  4. washthe precipitate was washed with 2-propanol (2×4 ml)
  5. customdried by suction

Sources & evidence

ORD record
ord-aa41ca1e747d4955a962b5695831aad2
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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