Pyridine → Benzophenone oxime

HRID 273668

Reaction equation

HRID 273668 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][OH:17].N1C=CC=CC=1>C(O)C>[C:1](=[N:16][OH:17])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 3102BenzophenoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 11324Benzophenone oximeYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of benzophenone (10.0 g), hydroxylamine hydrochloride (10.0 g), pyridine (50 ml), and absolute ethanol (50 ml) was pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa). The effluent was cooled and the solvent removed by rotary evaporation, and the residue stirred with cold water (50 ml). The crued oxime was filtered off and recrystallised from ethanol to afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5 for a batchwise preparation by microwave heating.

Workup

  1. customwas pumped through the CMR (15 ml/min; 155°-60° C., 700 kPa)
  2. temperatureThe effluent was cooled
  3. customthe solvent removed by rotary evaporation
  4. filtrationThe crued oxime was filtered off
  5. customrecrystallised from ethanol
  6. customto afford pure product (8.0 g; 73% yield), m.p. 140.5°-141° C., cf lit.5
  7. customfor a batchwise preparation by microwave
  8. temperatureheating

Sources & evidence

ORD record
ord-ac558e05036749a489f53ea207276d67
Source dataset
uspto-grants-1995_02
Patent number
US05387397

Linked notes

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