Acetic Acid → HCID 178476845, compound

HRID 1197748Notes

Reaction equation

HRID 1197748 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:2].[C:18]([NH:26][NH2:27])(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.C(O)(=O)C>C(O)C>[C:18](=[N:26][NH2:27])([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[N:21][CH:20]=1.[CH:1]([C:3]1[CH:17]=[CH:16][CH:15]=[CH:14][C:4]=1[CH2:5][P:6](=[O:13])([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 11112Nicotinic acid, hydrazideHCID 19104780Diethyl 2-formylbenzylphosphonate

Product 1

HCID 178476845HCID 178476845, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.0 g (8 mmol) of the compound A and 1.07 g (8 mmol) of nicotinic acid hydrazide were dissolved in 30 ml of absolute ethanol. After adding 1 ml of acetic acid, the mixture was boiled under reflux for 8 h. The solvent was removed by rotary evaporation and the residue was chromatographed on silica gel (eluent CH2Cl2 /EtOH 9.5/0.5; Rf =0.45). The product E was obtained in crystalline form. Yield: 2.2 g (73%); m.p.: 136° to 140° C.;

Workup

  1. temperatureunder reflux for 8 h
  2. customThe solvent was removed by rotary evaporation
  3. customthe residue was chromatographed on silica gel (eluent CH2Cl2 /EtOH 9.5/0.5

Sources & evidence

ORD record
ord-2469b6a0d38d4788b7fbcc01519729ce
Source dataset
uspto-grants-1994_01
Patent number
US05278152

Reaction notes

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