3-Chloro-6-hydroxyacetophenone → HCID 136265212, compound

HRID 877622Notes

Reaction equation

HRID 877622 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.[O:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([NH:23][NH2:24])=[O:22])[CH2:14][CH2:13]1>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]=[CH:26][CH:27]=[C:18]([N:15]3[CH2:16][CH2:17][O:12][CH2:13][CH2:14]3)[CH:19]=2)/[CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 71483853-Morpholin-4-yl-benzoic acid hydrazide

Product 1

HCID 136265212HCID 136265212, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

1-(5-Chloro-2-hydroxyphenyl)ethanone (40 mg, 0.234 mmol) and 3-morpholinobenzohydrazide (51.9 mg, 0.234 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 (60 mg) as a solid. 1H NMR (400 MHz, DMSO-d6): δ 7.65 (d, 1H, J=2.4 Hz), 7.42-7.32 (m, 4H), 7.20 (m, 1H), 6.94 (d, 1H, J=8.8 Hz), 3.77 (m, 4H), 3.19 (m, 4H), 2.48 (s, 3H). ESI-MS: 374.1 [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-af7dd00f40914f52b4df816035f74be3
Source dataset
uspto-grants-2015_03
Patent number
US08987335B2

Reaction notes

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