Acetic Acid → HCID 4330068, compound

HRID 967106Notes

Reaction equation

HRID 967106 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[C:11]([O:16][CH2:17][CH3:18])(=[O:15])[C:12]([CH3:14])=O.C(O)(=O)C>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:12]([CH3:14])[C:11]([O:16][CH2:17][CH3:18])=[O:15])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 12041Ethyl pyruvateHCID 121574-Bromophenylhydrazine hydrochloride

Product 1

HCID 4330068HCID 4330068, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromophenylhydrazine hydrochloride (15 g), ethyl pyruvate (11 ml) and acetic acid (1 ml) were dissolved in ethanol and heated to reflux for 2 hours, then cooled to room temperature, resulting in precipitation of a yellow solid, which was filtered off and dried in vacuo to give the ethyl pyruvate 4-bromophenylhydrazone (16.3 g, 71%), mp 153-154°; NMR δ (CD3SOCD3) 1.23 (t, 3H), 2.03 (s, 3H), 4.18 (q, 2H), 7.19 (d, 2H), 7.40 (d, 2H), 9.88 (brs, 1H); M/z (−) 285 (M+), 283, 171, 169, 113.

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 hours
  3. customresulting in precipitation of a yellow solid, which
  4. filtrationwas filtered off
  5. customdried in vacuo

Sources & evidence

ORD record
ord-b1895f9169974ade8fe8cd4d0fdd576f
Source dataset
uspto-grants-2005_10
Patent number
US06953809B2

Reaction notes

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