4-Hydroxybenzoic acid hydrazide → HCID 136341167, compound

HRID 1667563Notes

Reaction equation

HRID 1667563 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.[CH3:12][C:13]1[CH:17]=[C:16]([CH3:18])[NH:15][C:14]=1[CH:19]=O>C(O)(=O)C.CCO>[CH3:12][C:13]1[CH:17]=[C:16]([CH3:18])[NH:15][C:14]=1[CH:19]=[N:9][NH:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 17424-Hydroxybenzoic acid hydrazideHCID 2704653,5-Dimethyl-1H-pyrrole-2-carbaldehyde

Product 1

HCID 136341167HCID 136341167, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-benzoic acid hydrazide (0.3 g, 0.002 mol) and 3,5-dimethyl-pyrrole-2-carboxaldehyde (0.25 g, 0.002 mol) in abs. EtOH (10 mL), was added 1 drop of acetic acid. The reaction mixture was refluxed for 5 hours. The reaction mixture was cooling to room temperature and concentrated to remove solvent. The resulting residue was solidified by EtOAc to give grey solid 0.44 g, in 86% yield, mp: 261.2° C. 1H NMR (CD3OD) δ 8.12 (s, 1H), 7.79 (d, 2H), 6.88 (d, 2H), 5723 (s, 1H), 2.24 (s, 3H), 2.13 (s, 3H). 13C NMR (CD3OD) δ 166.5, 162.5, 139.4, 134.1, 130.5, 127.1, 124.9, 124.1, 116.3, 110.7, 12.9, 10.7. Anal. Calcd for C14H15N3O2: C, 65.35; H, 5.88; N, 16.33. Found: C, 65.52; H, 5.79; N, 16.30.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. concentrationconcentrated
  3. customto remove solvent

Sources & evidence

ORD record
ord-c38ba19b33474b6c9f2eea8f7d36323b
Source dataset
uspto-grants-2011_10
Patent number
US08044241B2

Reaction notes

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