Methane → HCID 136393716, compound

HRID 247742Notes

Reaction equation

HRID 247742 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11](=O)[CH2:12][CH3:13])[CH:6]=[C:7]([Br:10])[C:8]=1[OH:9].Cl.[CH3:16][O:17][NH2:18].C(O)C.C>N1C=CC=CC=1>[CH3:16][O:17][N:18]=[C:11]([C:5]1[CH:6]=[C:7]([Br:10])[C:8]([OH:9])=[C:3]([CH2:2][NH2:1])[CH:4]=1)[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 297MethaneHCID 702EthanolHCID 521874O-Methylhydroxylamine hydrochlorideHCID 13913247HCID 13913247, compound

Product 1

HCID 136393716HCID 136393716, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 9.0 g of 3'-aminomethyl-5'-bromo-4'-hydroxypropiophenone and 9.0 g of O-methylhydroxylamine hydrochloride in 80 ml of pyridine and 40 m of ethanol is refluxed with heating for 25 minutes. Activated charcoal is added to the reaction mixture and then filtered off. The filtrate is concentrated under reduced pressure and to the residue are added 200 ml of ice-cold water and 6.0 g of sodium hydrogencarbonate and stirred. The insoluble substance is collected by filtration and washed with water and then dried to give 7.9 g of 3'-aminomethyl-5'-bromo-4'-hydroxypropiophenone O-methyloxime as fine powdery solid, melting at 178°-178.5° C. with decomposition.

Workup

  1. temperaturewith heating for 25 minutes
  2. filtrationfiltered off
  3. concentrationThe filtrate is concentrated under reduced pressure and to the residue
  4. additionare added 200 ml of ice-cold water and 6.0 g of sodium hydrogencarbonate
  5. filtrationThe insoluble substance is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-dd791c9c57ef4f06a88791d99c997de1
Source dataset
uspto-grants-1987_11
Patent number
US04709095

Reaction notes

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