3-Chloro-6-hydroxyacetophenone → Kdm1A-IN-29

HRID 1777052Notes

Reaction equation

HRID 1777052 reaction equation
[NH:1]([C:3]([C:5]1[CH:6]=[C:7]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=1)=[O:4])[NH2:2].[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21]([C:23](=O)[CH3:24])[CH:22]=1>CO.C(O)(=O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([OH:26])=[C:21](/[C:23](=[N:2]/[NH:1][C:3]([C:5]2[CH:6]=[C:7]([S:11]([NH:14][CH3:15])(=[O:13])=[O:12])[CH:8]=[CH:9][CH:10]=2)=[O:4])/[CH3:24])[CH:22]=1

Participants

5

Reactant 2

HCID 740613-Chloro-6-hydroxyacetophenoneHCID 677513503-(hydrazinecarbonyl)-N-methylbenzenesulfonamide

Product 1

HCID 136265204Kdm1A-IN-29Yield 36.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

3-(hydrazinecarbonyl)-N-methylbenzenesulfonamide (120 mg, 0.523 mmol) and 1-(5-chloro-2-hydroxyphenyl)ethanone (89 mg, 0.523 mmol) was dissolved in Methanol (Volume: 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. Reaction was monitored by TLC. After completion of the reaction, following cooling, the solvent was removed by vacuum and the resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) afforded the title compound (E)-3-(2-(1-(5-chloro-2-hydroxyphenyl)ethylidene)hydrazinecarbonyl)-N-methylbenzenesulfonamide (75 mg, 0.192 mmol, 36.8% yield) as a solid. 1H NMR (CDCl3, 400 MHz): δ 8.21 (m, 1H), 8.06 (m, 1H), 7.95 (d, 1H, J=7.6 Hz), 7.59 (t, 1H, J=8.0 Hz), 7.39 (d, 1H, J=2.4 Hz), 7.18 (m, 1H), 6.90 (d, 1H, J=8.0 Hz), 2.56 (s, 3H), 2.36 (5, 3H). Mass [M+H]+: 382.1

Workup

  1. customReaction
  2. customAfter completion of the reaction
  3. temperaturefollowing cooling
  4. customthe solvent was removed by vacuum
  5. customthe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-46b632af9d8d4a8c92696f20710853cb
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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