Methyl 4-nitrobutyrate → HCID 19075158, compound

HRID 1600201Notes

Reaction equation

HRID 1600201 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 reflux 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, elutingwith 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. temperatureat reflux for 6 hours
  3. concentrationthe mixture was concentrated
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue purified by flash column chromatography, elutingwith 1:49 methanol/chloroform

Sources & evidence

ORD record
ord-250f255a2add47c4b8d12cf1cac67677
Source dataset
uspto-grants-1998_04
Patent number
US05744480

Reaction notes

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