Phenylhydrazine → HCID 178515239, compound

HRID 2271091Notes

Reaction equation

HRID 2271091 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:19]1([NH:25][NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)CCC>[C:19]1([N:25]2[C:8](=[O:10])[C:7]3=[CH:6][NH:5][CH:4]=[C:3]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:2]3=[N:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 7516Phenylhydrazine2×HCID 10901406HCID 10901406, compound

Product 1

HCID 178515239HCID 178515239, compoundYield 9.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 4-chloro-3-phenyl-5-pyridinecarboxylate (0.300 g, 1.15 mmol) and phenylhydrazine (0.125 ml, 1.27 mmol) in 1-butanol (25 ml) was stirred at reflux under nitrogen for 24 h. More phenylhydrazine (0.125 ml, 1.27 mmol) was added and the mixture was stirred at reflux for a further 3 days. The solvent was removed in vacuo and dichloromethane, followed by hydrogen chloride in diethyl ether, was added. The solution was filtered, and the filtrate was washed with aqueous NaHCO3 and evaporated in vacuo to give 31 mg (9%) of the title compound as a yellow solid; mp 280-285° C.; 1H NMR (250 MHz, DMSO-d6) δ7.18 (1H, t, J 7.4 Hz), 7.41-7.56 (5H, m), 7.91 (1H, s), 8.17 (2H, d, J 7.1 Hz), 8.22 (2H, d, J 7.5 Hz), 8.58 (1H, s), 12.60 (1H, br s); MS (ES+) m/z 288 [MH]+. Anal. found: C, 70.03; H, 5.00; N, 13.41. C18H12N3O.1.3H2O requires: C, 69.80; H, 4.75; N, 13.56%.

Workup

  1. temperatureat reflux under nitrogen for 24 h
  2. stirringthe mixture was stirred
  3. temperatureat reflux for a further 3 days
  4. customThe solvent was removed in vacuo and dichloromethane
  5. additionwas added
  6. filtrationThe solution was filtered
  7. washthe filtrate was washed with aqueous NaHCO3
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-b0fe543da10741fab8a791be70265993
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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