Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1) → HCID 178439621, compound

HRID 2271094Notes

Reaction equation

HRID 2271094 reaction equation
[Cl:1][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].Cl.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1>C(O)CCC>[ClH:1].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]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:25]2)=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 18329980HCID 18329980, compound

Product 1

HCID 178439621HCID 178439621, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 4-chloro-3-propyl-5-pyridinecarboxylate (0.3199 g, 1.40 mmol) and 4-chlorophenylhydrazine hydrochloride (0.3019 g, 1.69 mmol) in anhydrous 1-butanol (12 ml) was degassed by evaporating the flask under vacuum and refilling with nitrogen several times and then stirred at reflux under nitrogen for 4 h. After leaving to cool overnight, the mixture was filtered, and the solid was washed with ethyl acetate and dried at 60° C. under vacuum to afford 0.2454 g (54%) of the title compound as a yellow solid; mp 213-218° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ0.94 (3H, t, J 7.4 Hz), 1.76 (2H, m), 2.64 (2H, t, J 7.3 Hz), 7.41 (1H, s), 7.48 (2H, d, J 9.0 Hz), 8.24 (2H, d, J 8.9 Hz), 8.52 (1H, s), 12.36 (1H, br s); MS (ES+) m/z 288/290 [MH]+. Anal. found: C, 56.13; H, 4.64; N, 13.02. C15H14CIN3O.0.9HCl requires: C, 56.20; H, 4.69; N, 13.11%.

Workup

  1. customwas degassed
  2. customby evaporating the flask under vacuum
  3. temperatureat reflux under nitrogen for 4 h
  4. customAfter leaving
  5. temperatureto cool overnight
  6. filtrationthe mixture was filtered
  7. washthe solid was washed with ethyl acetate
  8. customdried at 60° C. under vacuum

Sources & evidence

ORD record
ord-7e87de784faf4830bd7cc2460703177c
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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