Acetic Acid → HCID 85029933, compound

HRID 335676Notes

Reaction equation

HRID 335676 reaction equation
[CH2:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1)[CH3:2].C(O)(=O)C.[CH:17](=O)[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CO>[C:20]1([CH2:19][CH2:18][CH:17]=[N:10][NH:9][C:7](=[O:8])[C:6]2[CH:11]=[CH:12][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7707BenzenepropanalHCID 3146404-ethylbenzohydrazide

Product 1

HCID 85029933HCID 85029933, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-ethyl-benzoic acid hydrazide (10 g, 60.9 mmoles) was dissolved in 32 mL of methanol. Acetic acid (1 mL) was added, the mixture was brought to reflux, and hydrocinnamaldehyde (5.77 g, 67 mmoles) was then slowly added. The reaction mixture was refluxed for 10 h and monitored by TLC. The precipitates were collected via filtration and washed with hexanes. 4-Ethyl-benzoic acid (3-phenyl-propylidene)-hydrazide was obtained as a white solid (9.34 g, 54.7% yield). Rf=0.36 (1:1 EtOAc:n-hexane); 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 7.72-7.24 (m, 10H), 2.87 (t, J=15.2 Hz, 2H), 2.79-2.57 (m, 4H), 1.24 (t, J=8 Hz, 3H).

Workup

  1. temperatureto reflux
  2. temperatureThe reaction mixture was refluxed for 10 h
  3. filtrationThe precipitates were collected via filtration
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-08069ed6e927498d972420c4d820cc07
Source dataset
uspto-grants-2014_11
Patent number
US08884060B2

Reaction notes

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