4-Ethylaniline → HCID 178436606, compound

HRID 253694Notes

Reaction equation

HRID 253694 reaction equation
[CH2:1]([C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1)[CH3:2].[CH3:10][O:11][C:12](=[O:25])[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([C:20](Cl)=[N:21][OH:22])[C:14]=1[F:24]>C1COCC1>[CH3:10][O:11][C:12](=[O:25])[C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([C:20](=[N:21][OH:22])[NH:7][C:6]2[CH:8]=[CH:9][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=2)[C:14]=1[F:24]

Participants

4

Reactant 2

HCID 115044-EthylanilineHCID 72566916Methyl-6-chloro-3-(chloro(hydroxyimino)methyl)-2-fluorobenzoate

Product 1

HCID 178436606HCID 178436606, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Ethylaniline (923 μl, 7423 μmol) was added dropwise to a 0° C. chilled solution of methyl-6-chloro-3-(chloro(hydroxyimino)methyl)-2-fluorobenzoate (395 mg, 1485 μmol) in anhydrous THF (4.5 ml). The resultant mixture was stirred for one hour before the ice bath was removed and the mixture was allowed to warm to RT. After stirring for several hours at RT, LCMS analysis indicated the reaction was complete. The solvent was removed solvent in vacuo and the brown residue was diluted with brine and EtOAc. The layers were separated and the aqueous was extracted with EtOAc (3×). The combined organics were dried over MgSO4, filtered and concentrated to a brown oil which was purified by silica gel chromatography using 2:1 Hex/EtOAc to afford the desired product.

Workup

  1. customwas removed
  2. customThe solvent was removed solvent in vacuo
  3. additionthe brown residue was diluted with brine and EtOAc
  4. customThe layers were separated
  5. extractionthe aqueous was extracted with EtOAc (3×)
  6. dry with materialThe combined organics were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to a brown oil which
  9. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-2531b5892d584699bb9eaed224025357
Source dataset
uspto-grants-2011_01
Patent number
US07872128B2

Reaction notes

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