4-Hydroxybenzoic acid hydrazide → HCID 789070, compound

HRID 1985013Notes

Reaction equation

HRID 1985013 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.[C:12]1([CH3:20])[CH:17]=[CH:16][C:15]([CH:18]=O)=[CH:14][CH:13]=1>C(O)(=O)C.CCO>[CH3:20][C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[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:13]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 77254-Methylbenzaldehyde

Product 1

HCID 789070HCID 789070, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-benzoic acid hydrazide (0.3 g, 0.002 mol) in abs. EtOH (10 mL) and p-tolualdehyde (0.24 g, 0.002 mol) 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 0.49 g, in 96% yield, mp: 252.6° C. 1H NMR (CD3OD) δ 8.26 (s, 1H), 7.82 (d, 2H), 7.70 (d, 2H), 7.24 (d,2H), 6.88 (d, 2H), 2.36 (s, 3H). 13C NMR (CDCl3) δ 166.8, 162.7, 150.0, 142.0, 132.0, 130.5, 128.8, 124.7, 116.3, 21.5. Anal. Calcd for C14H12N2O2: C, 69.99; H, 5.03; N, 11.66. Found: C, 70.01; H, 5.08; N, 11.73.

Workup

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

Sources & evidence

ORD record
ord-8d3599c80f5e4b7d88dce212f322c68b
Source dataset
uspto-grants-2009_06
Patent number
US07544838B2

Reaction notes

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