3,5-Difluoroaniline → HCID 68684330, compound

HRID 1171084Notes

Reaction equation

HRID 1171084 reaction equation
O=[C:2]([CH2:13][CH3:14])[CH:3]([CH2:9][C:10](=O)[CH3:11])[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:15][C:16]1[CH:17]=[C:18]([CH:20]=[C:21]([F:23])[CH:22]=1)[NH2:19]>C(O)(=O)C>[F:15][C:16]1[CH:17]=[C:18]([N:19]2[C:10]([CH3:11])=[CH:9][C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]2[CH2:13][CH3:14])[CH:20]=[C:21]([F:23])[CH:22]=1

Participants

4

Reactant 2

HCID 965953,5-DifluoroanilineHCID 12699551HCID 12699551, compound

Product 1

HCID 68684330HCID 68684330, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

Ethyl 3-oxo-2-(2-oxopropyl)pentanoate (200 mg) and 3,5-difluoroaniline (380 mg) were dissolved in acetic acid (10 mL), and stirred at 80° C. for 2.5 hours. The reaction liquid was cooled to room temperature, then the solvent was evaporated off, the residue was diluted with chloroform, and washed with aqueous saturated sodium hydrogencarbonate solution. The extract was washed with saturated saline water, then dried with anhydrous sodium sulfate, then the solvent was evaporated off, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1) to obtain the entitled compound (287 mg) as a pale yellow oil.

Workup

  1. customThe reaction liquid
  2. temperaturewas cooled to room temperature
  3. customthe solvent was evaporated off
  4. additionthe residue was diluted with chloroform
  5. washwashed with aqueous saturated sodium hydrogencarbonate solution
  6. washThe extract was washed with saturated saline water
  7. dry with materialdried with anhydrous sodium sulfate
  8. customthe solvent was evaporated off
  9. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-ffbc75a772864cecb37c48c79796bc40
Source dataset
uspto-grants-2010_11
Patent number
US07829586B2

Reaction notes

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