3-Chloro-6-hydroxyacetophenone → HCID 136491217, compound

HRID 1777038Notes

Reaction equation

HRID 1777038 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.[CH3:12][S:13]([C:16]1[CH:17]=[N:18][CH:19]=[C:20]([CH:25]=1)[C:21]([NH:23][NH2:24])=[O:22])(=[O:15])=[O:14]>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](/[C:8](=[N:24]/[NH:23][C:21](=[O:22])[C:20]2[CH:25]=[C:16]([S:13]([CH3:12])(=[O:15])=[O:14])[CH:17]=[N:18][CH:19]=2)/[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 71258130HCID 71258130, compound

Product 1

HCID 136491217HCID 136491217, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(5-Chloro-2-hydroxyphenyl)ethanone (50 mg, 0.293 mmol) and 5-(methylsulfonyl) nicotinohydrazide (63.1 mg, 0.293 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 (3% CH3OH/CH2Cl2) affording the title compound (70 mg, 63.0% yield) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 11.86 (s, 1H), 9.37 (s, 1H), 9.27 (s, 1H), 8.76 (s, 1H), 7.68 (s, 1H), 7.36 (d, 1H, J=8.8 Hz), 6.97 (d, 1H, J=8.8 Hz), 3.42 (s, 3H), 2.53 (s, 3H). ESI-MS: 368.8 [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 (3% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-ef2f48924fb04cd0b408006ef31f9704
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

Loading…