Hydrochloric Acid → HCID 73461926, compound

HRID 434031Notes

Reaction equation

HRID 434031 reaction equation
Cl[C:2]1[CH:9]=C[CH:7]=[C:6]([F:10])[C:3]=1C=O.[ClH:11].[NH2:12][OH:13].[OH-].[Na+].Cl.[CH3:17][CH2:18]O>O>[Cl:11][C:17]1[CH:18]=[CH:7][C:6]([F:10])=[CH:3][C:2]=1[CH:9]=[N:12][OH:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium Hydroxide2×HCID 678472-Chloro-6-fluorobenzaldehydeHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 73461926HCID 73461926, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-chloro-6-fluorobenzaldehyde (15.0 g, 94.6 mmol) and hydroxylamine hydrochloride (7.90 g, 114 mmol) in EtOH (25 ml), H2O (25 ml), and ice (40 g) was added NaOH (19 ml, 50% wt. solution). Ice was added during the addition of the NaOH to maintain the reaction temperature below 40 degrees C. The mixture was stirred at room temperature for 1 h. Ice was added, the pH adjusted to 6 with HCl (2 N), and extracted twice with Et2O. The combined Et2O layers were washed (brine) and dried (MgSO4). Filtration and concentration gave a yellow-brown solid that was recrystallized from Et2O/hexanes to give 2-chloro-5-fluorobenzaldehyde oxime (12.2 g, 74%).

Workup

  1. temperatureto maintain the reaction temperature below 40 degrees C
  2. additionIce was added
  3. extractionextracted twice with Et2O
  4. washThe combined Et2O layers were washed (brine)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration
  7. customgave a yellow-brown solid that
  8. customwas recrystallized from Et2O/hexanes

Sources & evidence

ORD record
ord-45d14117340c4adbb7daa0bb6bf6b399
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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