Ammonium Acetate → HCID 49817597, compound

HRID 2061005Notes

Reaction equation

HRID 2061005 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH2:10][C:11](=O)[CH2:12][C:13]([O:15][CH3:16])=[O:14].C([O-])(=O)C.[NH4+:22]>CO>[CH3:16][O:15][C:13](=[O:14])/[CH:12]=[C:11](\[NH2:22])/[CH2:10][C:3]1[CH:4]=[C:5]([F:9])[C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 29942605Methyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate

Product 1

HCID 49817597HCID 49817597, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-(2,4,5-trifluorophenyl)acetoacetate from Example 1 (25.0 g, 102 mmol) and ammonium acetate (38.5 g, 500 mmol) in methanol (250 ml) was stirred at reflux until the starting material totally disappeared (˜4 h). The whole reaction mixture was then concentrated, switched to dichloromethane and filtered. The filtration was washed with water, then brine, then dried over sodium sulfate, filtered and evaporated—ed. The residue oil solidified when hexane was added. The solid was collected by filtration and dried to give 22.4 g of the enamine product (89.6%). 1H NMR (300 MHz, CDCl3) 7.12-7.03 (m, 1H), 6.99-6.90 (m, 1H), 4.56 (s, 1H) 3.65 (s, 3H), 3.40 (s, 2H)

Workup

  1. temperatureat reflux until the starting material
  2. custom(˜4 h)
  3. customThe whole reaction mixture
  4. concentrationwas then concentrated
  5. filtrationfiltered
  6. filtrationThe filtration
  7. washwas washed with water
  8. dry with materialbrine, then dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated—ed
  11. additionwas added
  12. filtrationThe solid was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-0e4b2cda71414bf89e7275a30c04faa7
Source dataset
uspto-grants-2012_10
Patent number
US08278486B2

Reaction notes

Loading…