Phenylhydrazine → HCID 178439620, compound

HRID 2271093Notes

Reaction equation

HRID 2271093 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[CH:4][C:3]=1[CH2:13][CH2:14][CH3:15].[C:16]1([NH:22][NH2:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)CCC>[C:16]1([N:22]2[C:8](=[O:10])[C:7]3=[CH:6][NH:5][CH:4]=[C:3]([CH2:13][CH2:14][CH3:15])[C:2]3=[N:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 18329980HCID 18329980, compound

Product 1

HCID 178439620HCID 178439620, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate (0.5123 g, 2.25 mmol) and phenylhydrazine (0.32 ml, 3.25 mmol) in anhydrous 1-butanol (18 ml) was stirred at reflux under nitrogen for 50 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2) to give 0.4767 g (84%) of the title compound as a yellow solid; mp 221-224° C. (CH2Cl2-EtOAc-hexane); 1H NMR (360 MHz, DMSO-d6) δ0.95 (3H, t, J 7.3 Hz), 1.77 (2H, m), 2.63 (2H, t, J 7.3 Hz), 7.15 (1H, t, J 7.4 Hz), 7.36 (1H, s), 7.42 (2H, t, J 7.4 Hz), 8.19 (2H, d, J 7.5 Hz), 8.47 (1H, s), 12.14 (1H, br s); MS (ES+) m/z 254 [MH]+. Anal. found: C, 71.22; H, 5.59; N, 16.45. C15H15N3O requires: C, 71.13; H, 5.97; N, 16.59%.

Workup

  1. temperatureat reflux under nitrogen for 50 h
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-4d1a89d7df3f4079a4c0719115377628
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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