4-Methoxyphenylhydrazine hydrochloride → HCID 178488389, compound

HRID 2271105Notes

Reaction equation

HRID 2271105 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10]CC)=O)=[CH:6][N:5]=[C:4]([CH3:13])[C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.Cl.[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([NH:31][NH2:32])=[CH:27][CH:26]=1>C(O)CCC>[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([N:31]2[C:8](=[O:10])[C:7]3=[CH:6][NH:5][C:4]([CH3:13])=[C:3]([C:14]4[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=4)[C:2]3=[N:32]2)=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochloride2×HCID 18329922HCID 18329922, compound

Product 1

HCID 178488389HCID 178488389, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethyl 4-chloro-3-(4-methoxyphenyl)-2-methyl-5-pyridinecarboxylate (0.1842 g, 0.602 mmol) and 4-methoxyphenylhydrazine hydrochloride (0.1000 g, 0.724 mmol) in anhydrous 1-butanol (7 ml) was degassed by evaporating the flask under vacuum and refilling with nitrogen several times. The mixture was then stirred at reflux under nitrogen for 32 h, during which time more 4-methoxyphenylhydrazine hydrochloride (0.1001 g, 0.724 mmol) was added. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 3-7% MeOH/CH2Cl2) to give 45.5 mg (21%) of the title compound as a yellow solid; mp 274-282° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ2.40 (3H, s), 3.88 (3H, s), 3.96 (3H, s), 7.08 (2H, d, J 9.2 Hz), 7.19 (2H, d, J 8.7 Hz), 7.59 (2H, d, J 8.7 Hz), 8.11 (2H, d, J 9.1 Hz), 8.61 (1H, s), 12.43 (1H, br s); MS (ES+) m/z 362 MH]+. Anal. found: C, 69.95; H, 5.02; N, 11.60. C21H19N3O3 requires: C, 69.79; H, 5.30; N, 11.63%.

Workup

  1. customwas degassed
  2. customby evaporating the flask under vacuum
  3. additionwas added
  4. customThe solvent was removed in vacuo
  5. customthe residue was purified by flash chromatography (silica gel, 3-7% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-1147efddcf5947c7a9ebd678f993741f
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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