Dichloromethane → 3-bromo-5-[(E)-C-[(2R)-2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

HRID 1617784Notes

Reaction equation

HRID 1617784 reaction equation
[Br:1][C:2]1[C:3](=[O:27])[N:4]([CH3:26])[CH:5]=[C:6]([C:8](=O)[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:7]=1.C(=O)(O)[O-].[Na+].Cl.[NH2:34][OH:35].ClCCl>C(O)C.O>[Br:1][C:2]1[C:3](=[O:27])[N:4]([CH3:26])[CH:5]=[C:6](/[C:8](=[N:34]/[OH:35])/[CH2:9][C@H:10]([C:18]2[CH:23]=[CH:22][C:21]([Br:24])=[CH:20][CH:19]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH:7]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67015677(R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 580433643-bromo-5-[(E)-C-[(2R)-2-(4-bromophenyl)-2-(2-methylphenyl)ethyl]-N-hydroxycarbonimidoyl]-1-methylpyridin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of (R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one in ethanol (2.5 mL) and water (0.1 mL) were added sodium bicarbonate (30.9 mg) and hydroxylamine hydrochloride (32.0 mg) and the reaction mixture was stirred at reflux (100° C. oil bath temperature) for 2 hours. The reaction mixture was poured on water and dichloromethane and the layers were separated. The aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with brine, dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography using a MPLC system (10 g silica gel column, CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane/ethyl acetate (100:0 to 50:50) to give the title compound as a white solid, MS (ESI+): m/z=504.99 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted twice with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by silica gel chromatography
  9. washeluting with a gradient of n-heptane/ethyl acetate (100:0 to 50:50)

Sources & evidence

ORD record
ord-fe25111cb05e4354931e3a6f78d50c20
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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