Hydroxylamine → Ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

HRID 1846107Notes

Reaction equation

HRID 1846107 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH:12]=O)[C:6]=1[F:14])[CH3:2].[NH2:16][OH:17]>CO>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[C:10]([Cl:11])=[CH:9][CH:8]=[C:7]([CH:12]=[N:16][OH:17])[C:6]=1[F:14])[CH3:2]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 58483266HCID 58483266, compound

Product 1

HCID 76800184Ethyl 6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 6-chloro-2-fluoro-3-formyl-benzoic acid ethyl ester (4.04 g; 17.52 mmol), hydroxylamine (50% aq. solution, 4.29 mL; 70 mmol) in MeOH (60 mL) was stirred at 55° C. for 1.5 h. The mixture was concentrated i. vac., diluted with EtOAc, washed with brine, dried over Na2SO4 and concentrated i.vac. to furnish the subtitle compound.

Workup

  1. concentrationThe mixture was concentrated i
  2. addition, diluted with EtOAc
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated i.vac

Sources & evidence

ORD record
ord-dd0871d3f04b4e3790673be115def190
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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