Methyl 4-nitrobutyrate → HCID 19075158, compound

HRID 965014Notes

Reaction equation

HRID 965014 reaction equation
[F:1][C:2]([F:13])([F:12])[O:3][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O.C([O-])(=O)C.[NH4+:18].[N+:19]([CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=O)([O-:21])=[O:20]>C(O)C>[N+:19]([CH:22]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([O:3][C:2]([F:13])([F:12])[F:1])[CH:5]=2)[NH:18][C:25](=[O:27])[CH2:24][CH2:23]1)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 25604Methyl 4-nitrobutyrateHCID 517165Ammonium AcetateHCID 6051393-(Trifluoromethoxy)benzaldehyde

Product 1

HCID 19075158HCID 19075158, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, in a round-bottom flask were placed 15 g (79 mmol) of 3-trifluoromethoxybenzaldehyde, 80 mL of ethanol, 11 g (0.26 mol) of ammonium acetate and 12.6 mL (79 mmol) of methyl 4-nitrobutyrate, and the mixture was heated at ref lux for 6 hours. After cooling to room temperature, the mixture was concentrated. The remaining material was stirred with ca. 200 mL of CHCl3 for 30 minutes, filtered and concentrated. The residue purified by flash column chromatography, eluting with 1:49 methanol/chloroform followed by 1:19 methanol/chloroform to obtain 24 g of 5-nitro-6-(3-trifluoromethoxyphenyl)piperidin-2-one.

Workup

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. concentrationthe mixture was concentrated
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue purified by flash column chromatography
  6. washeluting with 1:49 methanol/chloroform

Sources & evidence

ORD record
ord-4fc5c0d357c8475b8920165ec7c00953
Source dataset
uspto-grants-1998_06
Patent number
US05773450

Reaction notes

Loading…