Methane → HCID 136393715, compound

HRID 247741Notes

Reaction equation

HRID 247741 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.[NH2:16][OH:17].C>[OH-].[Na+].C(O)C>[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([C:11](=[N:16][OH:17])[CH2:12][CH3:13])[CH:6]=[C:7]([Br:10])[C:8]=1[OH:9]

Participants

6

Reactant 3

HCID 297MethaneHCID 443297Hydroxyamine hydrochlorideHCID 13913247HCID 13913247, compound

Product 1

HCID 136393715HCID 136393715, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 9.0 g of 3'-aminomethyl-5'-bromo-4'-hydroxypropiophenone and 7.0 g of hydroxylamine hydrochloride in 50 ml of 4N sodium hydroxide solution and 15 ml of ethanol is refluxed with heating for 40 minutes. To the reaction mixture is added activated charcoal and the charcoal is filtered off and then the mixture is adjusted to pH 6-7 with concentrated hydrochloric acid. After allowing to stand at room temperature, the precipitate is collected by filtration, washed with water and dried to give 8.1 g of 3'-aminomethyl-5'-bromo-4'-hydroxypropiophenone oxime, melting at 174°-175° C. with decomposition.

Workup

  1. temperaturewith heating for 40 minutes
  2. additionTo the reaction mixture is added
  3. filtrationthe charcoal is filtered off
  4. customto stand at room temperature
  5. filtrationthe precipitate is collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-d96c30ac82e6467cb44fcf0e0fd8a8b9
Source dataset
uspto-grants-1987_11
Patent number
US04709095

Reaction notes

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