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

HRID 59337Notes

Reaction equation

HRID 59337 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH:14]=O)=[CH:4][CH:3]=1.[OH:16][NH2:17]>CO>[Cl:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([F:13])[C:5]([CH:14]=[N:17][OH:16])=[CH:4][CH:3]=1

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
60 °C

Procedure

To a solution of ethyl 6-chloro-2-fluoro-3-formylbenzoate (1.1 g, 4.0 mmol) in MeOH (5 mL) was added (aq. solution) hydroxyl amine (4 mL) and the reaction mixture was heated at 60° C. for 2-3 h. The reaction mass was concentrated and extracted with EtOAC. The organic layer was washed with brine and concentrated to afford 0.900 g of the product. 1H NMR (300 MHz, DMSO d6): δ 1.31 (t, J=6.9 Hz, 3H), 4.40 (q, J=6.6 Hz, 2H), 7.47 (d, J=9.0 Hz, 1H), 7.86 (t, J=8.1 Hz, 1H), 8.20 (s, 1H), 11.89 (br s, 1H).

Workup

  1. concentrationThe reaction mass was concentrated
  2. extractionextracted with EtOAC
  3. washThe organic layer was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-bb66f1ca539d4c748cc1d09846d36591
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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