3-Chloro-6-hydroxyacetophenone → 3-bromo-4-chloro-N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]benzamide

HRID 877611Notes

Reaction equation

HRID 877611 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([NH:7][NH2:8])=[O:6].[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([OH:23])=[C:18]([C:20](=O)[CH3:21])[CH:19]=1>CO.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[Cl:12])[C:5]([NH:7]/[N:8]=[C:20](/[C:18]1[CH:19]=[C:14]([Cl:13])[CH:15]=[CH:16][C:17]=1[OH:23])\[CH3:21])=[O:6]

Participants

5

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 27355413-Bromo-4-chlorobenzhydrazide

Product 1

HCID 1362766193-bromo-4-chloro-N-[(E)-1-(5-chloro-2-hydroxyphenyl)ethylideneamino]benzamideYield 31.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

3-Bromo-4-chlorobenzohydrazide (30 mg, 0.120 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (20.51 mg, 0.120 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 (15 mg). 1H NMR (400 MHz, acetone-d6): δ 8.30 (s, 1H), 7.98 (d, 1H, J=8.4 Hz), 7.73 (d, 1H, J=8.4 Hz), 7.61 (d, 1H, J=2.4 Hz), 7.29 (dd, 1H, J=2.4 & 8.4 Hz), 6.93 (d, 1H, J=8.8 Hz), 2.55 (s, 3H). ESI-MS: 402.9 [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-fd6847ff24924314b88b7192d3e641b7
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

Loading…