Water → HCID 86246798, compound

HRID 2428087Notes

Reaction equation

HRID 2428087 reaction equation
[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=O.C([O-])(O)=O.[Na+].[OH2:17].[NH2:18]O.Cl>CC#N.CCCC[N+](CCCC)(CCCC)CCCC.[Cl-].CC(O)=O>[Cl:1][C:2]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([F:11])[C:3]=1[CH:4]=[N:18][OH:17]

Participants

8

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 27735092-Chloro-3,6-difluorobenzaldehyde

Product 1

HCID 86246798HCID 86246798, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-3,6-difluoro-benzaldehyde (25.0 g, 142 mmol) was dissolved in CH3CN (175 mL). To this sol. was added NaHCO3 (35.7 g, 424 mmol), and the mixture was stirred vigorously for 5 min. Water (350 mL) was added, and the mixture was stirred for 10 min. NH2OH.HCl (19.7 g, 283 mmol) and TBAC (1.97 g, 7.08 mmol) were added, and the reaction mixture was stirred at rt for 1 h. AcOH (20 mL) was added dropwise to pH 6-7. The mixture was extracted with Et2O (3×). The combined org. extracts were washed with brine, dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the title compound (25.0 g, 92%). LC-MS: tR=0.93 min.

Workup

  1. stirringthe mixture was stirred for 10 min
  2. stirringthe reaction mixture was stirred at rt for 1 h
  3. extractionThe mixture was extracted with Et2O (3×)
  4. washextracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customDrying under high vacuum

Sources & evidence

ORD record
ord-c5fb7753884a474aa3de81486b1f1201
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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