3-Amino-4-hydroxybenzohydrazide → 3-Amino-4-hydroxybenzoic Acid [4-(4-Isopropylbenzyloxy)-3,5-dimethoxybenzylidene]-hydrazide

HRID 1166777Notes

Reaction equation

HRID 1166777 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].[CH:13]([C:16]1[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]2[C:29]([O:30][CH3:31])=[CH:28][C:25]([CH:26]=O)=[CH:24][C:23]=2[O:32][CH3:33])=[CH:18][CH:17]=1)([CH3:15])[CH3:14]>CC(O)C>[CH:13]([C:16]1[CH:35]=[CH:34][C:19]([CH2:20][O:21][C:22]2[C:29]([O:30][CH3:31])=[CH:28][C:25]([CH:26]=[N:8][NH:7][C:5](=[O:6])[C:4]3[CH:9]=[CH:10][C:11]([OH:12])=[C:2]([NH2:1])[CH:3]=3)=[CH:24][C:23]=2[O:32][CH3:33])=[CH:18][CH:17]=1)([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 5858793-Amino-4-hydroxybenzohydrazideHCID 229993894-(4-Isopropylbenzyloxy)-3,5-dimethoxybenzaldehyde

Product 1

HCID 773009973-Amino-4-hydroxybenzoic Acid [4-(4-Isopropylbenzyloxy)-3,5-dimethoxybenzylidene]-hydrazideYield 103.6%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

The above 3-amino-4-hydroxybenzoic acid hydrazide (50 mg, 0.3 mmol) and the above 4-(4-isopropylbenzyloxy)-3,5-dimethoxybenzaldehyde(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 144 mg (100%) of the title compound as a solid. M.p.: 174-175° 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-46adebee2f9248d29a3e6c38ad090bbe
Source dataset
uspto-grants-2003_09
Patent number
US06613942B1

Reaction notes

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