3-Chloro-6-hydroxyacetophenone → 5-chloro-N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]pyridine-3-carboxamide

HRID 877618Notes

Reaction equation

HRID 877618 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([NH:9][NH2:10])=[O:8].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([OH:22])=[C:17]([C:19](=O)[CH3:20])[CH:18]=1>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7]([NH:9]/[N:10]=[C:19](/[C:17]1[CH:18]=[C:13]([Cl:12])[CH:14]=[CH:15][C:16]=1[OH:22])\[CH3:20])=[O:8]

Participants

5

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 144441945-Chloropyridine-3-carbohydrazide

Product 1

HCID 1362766215-chloro-N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]pyridine-3-carboxamideYield 35.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

5-Chloronicotinohydrazide (30 mg, 0.175 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (29.8 mg, 0.175 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. The reaction was monitored by TLC. Upon completion of the reaction and following cooling, the solvent was removed by vacuum, and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) affording the title compound as a solid (20 mg). 1H NMR (400 MHz, acetone-d6): δ 9.06 (s, 1H), 8.77 (s, 1H), 8.37 (s, 1H), 7.62 (d, 1H, J=2.8 Hz), 7.31 (dd, 1H, J=2.0 & 8.4 Hz), 6.95 (d, 1H, J=8.8 Hz), 2.58 (s, 3H). ESI-MS: 324.0 [M+H]+.

Workup

  1. customUpon completion of the reaction
  2. temperaturefollowing cooling
  3. customthe solvent was removed by vacuum
  4. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-30aa73d79e924cf589e5ee501f36b45d
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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