Ammonium Chloride → HCID 136166934, compound

HRID 1617613Notes

Reaction equation

HRID 1617613 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=O)=[CH:4][CH:3]=1.Cl.[NH2:27][OH:28].C([O-])(O)=O.[Na+].[Cl-].[NH4+]>C(O)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9]/[C:10](/[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:27]\[OH:28])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 67015589HCID 67015589, compound

Product 1

HCID 136166934HCID 136166934, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 3-(4-bromo-phenyl)-1-(4-hydroxy-phenyl)-3-o-tolyl-propan-1-one (16 mg), hydroxylamine hydrochloride (7 mg) and NaHCO3 (6.8 mg) in ethanol (0.455 ml) and water (0.016 ml) was heated to reflux for 2.5 h. After cooling to room temperature, a saturated aqueous solution of ammonium chloride was added and the mixture was extracted with dichloromethane. The organic phase was washed with brine, dried using MgSO4, filtered and concentrated to dryness. The product was purified by preparative TLC (SiO2, dichloromethane/methanol 9:1) to give the title compound containing less than 10% of the corresponding Z isomer (13 mg) as an off-white foam, MS (ESI+): m/z=408.1 [M−H]−.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2.5 h
  3. extractionthe mixture was extracted with dichloromethane
  4. washThe organic phase was washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe product was purified by preparative TLC (SiO2, dichloromethane/methanol 9:1)

Sources & evidence

ORD record
ord-9f9c094ba8e74320968dcc1b863c21b1
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

Loading…