4-Hydroxybenzoic acid hydrazide → 4-Hydroxy-N-[(4-methoxyphenyl)methylidene]benzene-1-carbohydrazonic acid

HRID 1985016Notes

Reaction equation

HRID 1985016 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][CH:3]=1.[CH:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1>C(O)(=O)C.CCO>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]=[N:9][NH:8][C:6](=[O:7])[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 312444-Methoxybenzaldehyde

Product 1

HCID 3100684-Hydroxy-N-[(4-methoxyphenyl)methylidene]benzene-1-carbohydrazonic acidYield 94.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxybenzhydrazide (0.3 g, 0.002 mol) and p-anisaldehyde (0.27 g, 0.002 mol) in abs. EtOH (10 mL) was added 1 drop of acetic acid. The reaction mixture was refluxed for 4 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give white solid 0.51 g, in 93% yield, mp: 209.0° C. 1H NMR (CD3OD) δ 8.23 (s, 1H), 7.82 (d, 2H), 7.76 (d, 2H), 6.97 (d,2H), 6.87 (d, 2H), 3.82 (s, 3H). 13C NMR (CD3OD) δ 166.8, 163.2, 162.7, 149.8, 130.8, 130.4, 128.2, 124.8, 116.3, 115.2, 55.9. Anal. Calcd for C15H14N2O3: C, 66.66; H, 5.22; N, 10.36. Found: C, 66.82; H, 5.28; N, 10.38.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated
  3. customto remove solvent

Sources & evidence

ORD record
ord-0ad26a8d0cec4b33885e835a99b1f4d9
Source dataset
uspto-grants-2009_06
Patent number
US07544838B2

Reaction notes

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