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

HRID 1777036Notes

Reaction equation

HRID 1777036 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-084f05ea3d92441b95d1609498fb5231
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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