Benzoylhydrazine → HCID 135578375, compound

HRID 877596Notes

Reaction equation

HRID 877596 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.[C:12]([NH:20][NH2:21])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO.C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6](/[C:8](=[N:21]/[NH:20][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)/[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 11955BenzoylhydrazineHCID 740613-Chloro-6-hydroxyacetophenone

Product 1

HCID 135578375HCID 135578375, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(5-Chloro-2-hydroxyphenyl)ethanone (100 mg, 0.586 mmol) and benzohydrazide (80 mg, 0.586 mmol) were dissolved in methanol (4 mL) in the presence of acetic acid as a catalyst, and then the reaction mixture was heated via microwave irradiation to 120° C. for 30 min. 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 (90 mg) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.95 (m, 2H), 7.67-7.62 (m, 2H), 7.56 (m, 2H), 7.35 (dd, 1H, J=2.4 & 8.8 Hz), 6.95 (d, 1H, J=8.4 Hz), 3.35 (s, 3H). ESI-MS: 289.0 [M+H]+.

Workup

  1. temperatureFollowing cooling
  2. customthe solvent was removed by vacuum
  3. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-7be9eb7c0d6b4dc7945c91cfaf8aa797
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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