Pyrrolidine → HCID 58980628, compound

HRID 1181923Notes

Reaction equation

HRID 1181923 reaction equation
[C:1]([CH:5]([CH:8]=O)[CH:6]=O)([CH3:4])([CH3:3])[CH3:2].[CH3:10][NH:11][C:12](=[O:17])[CH2:13][N+:14]([O-:16])=[O:15].N1CCCC1>C(O)C>[C:1]([C:5]1[CH:6]=[C:13]([N+:14]([O-:16])=[O:15])[C:12](=[O:17])[N:11]([CH3:10])[CH:8]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 574612tert-ButylpropanedialHCID 12512111N-Methylnitroacetamide

Product 1

HCID 58980628HCID 58980628, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-tert-butyl-malonaldehyde (385 mg, 3.00 mmol) and the above amide (355 mg, 3.00 mmol) dissolved in ethanol (6.0 mL) was added pyrrolidine (63 microL, 0.750 mmol). The mixture was heated at reflux for 18 h and concentrated in vacuo. Purification by silica-gel chromatography (75% ethyl acetate in hexanes) provided 5-tert-butyl-1-methyl-3-nitro-1H-pyridin-2-one (186 mg, 30%) as an orange solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. customPurification by silica-gel chromatography (75% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-bd365ee773104fb7a99758448f1a7250
Source dataset
uspto-grants-2007_10
Patent number
US07285545B2

Reaction notes

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