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

HRID 1695534Notes

Reaction equation

HRID 1695534 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([CH:11]=O)[C:5]=1[F:13].[NH2:15][OH:16]>C(O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[C:6]([CH:11]=[N:15][OH:16])[C:5]=1[F:13]

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59805812Methyl 6-chloro-2-fluoro-3-formylbenzoate

Product 1

HCID 72566917Methyl-6-chloro-2-fluoro-3-((hydroxyimino)methyl)benzoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl-6-chloro-2-fluoro-3-formylbenzoate (930 mg, 4294 μmol) in ethanol (14.5 ml) at RT was added hydroxylamine (50 wt. % aqueous solution) (1316 μl, 21469 μmol) and the solution was stirred for 16 hrs. The volatiles were removed by rotovap, the residue was diluted with water which caused a solid to precipitate. The solid was collected by filtration and washed with water and dried in vacuo to give the title compound as an off-white solid.

Workup

  1. customThe volatiles were removed by rotovap
  2. additionthe residue was diluted with water which
  3. customto precipitate
  4. filtrationThe solid was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-f4c5050517494c5d87850c5664e4ae8e
Source dataset
uspto-grants-2012_04
Patent number
US08163742B2

Reaction notes

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