Acetic Acid → HCID 85029933, compound

HRID 658567Notes

Reaction equation

HRID 658567 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-2019f38882fd425bb6237598e52df64c
Source dataset
uspto-grants-2011_12
Patent number
US08076517B2

Reaction notes

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