Methane → HCID 136393719, compound

HRID 247744Notes

Reaction equation

HRID 247744 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH3:13])[CH:6]=[C:7]([I:10])[C:8]=1[OH:9].Cl.[CH3:16][O:17][NH2:18].C>N1C=CC=CC=1.C(O)C>[CH3:16][O:17][N:18]=[C:11]([C:5]1[CH:6]=[C:7]([I:10])[C:8]([OH:9])=[C:3]([CH2:2][NH2:1])[CH:4]=1)[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 297MethaneHCID 521874O-Methylhydroxylamine hydrochlorideHCID 14014487HCID 14014487, compound

Product 1

HCID 136393719HCID 136393719, compoundYield 54.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1049PyridineSolvent

Procedure

To a solution of 2.0 g of 3'-aminomethyl-4'-hydroxy5'-iodopropiophenone in 15 ml of pyridine and 7 ml of ethanol is added 1.4 g of O-methylhydroxylamine hydrochloride, and the mixture is refluxed with heating for 45 minutes. The reaction mixture is treated with activated charcoal and filtered. The filtrate is concentrated under reduced pressure and to the residue is added ice-cold water. To the mixture is added 1.4 g of sodium hydrogencarbonate and stirred. The precipitated crystals are collected by filtration, washed with water and then recrystallized from methanol to give 1.2 g of 3'-aminomethyl-4'-hydroxy-5'-iodopropiophenone O-methyloxime, melting at 156°-157° C. with decomposition.

Workup

  1. temperaturethe mixture is refluxed
  2. temperaturewith heating for 45 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure and to the residue
  5. additionis added ice-cold water
  6. additionTo the mixture is added 1.4 g of sodium hydrogencarbonate
  7. filtrationThe precipitated crystals are collected by filtration
  8. washwashed with water
  9. customrecrystallized from methanol

Sources & evidence

ORD record
ord-cb393a96bdcc46eb87010e010096aa2c
Source dataset
uspto-grants-1987_11
Patent number
US04709095

Reaction notes

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