3-Nitrobenzaldehyde → t-butyl 2-[N-[2-(3-nitrobenzylidene)-3-oxobutanoyl]amino]acetate

HRID 342874Notes

Reaction equation

HRID 342874 reaction equation
[O:1]=[C:2]([CH3:15])[CH2:3][C:4]([NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5].[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=O)([O-:18])=[O:17]>C(O)(C)C.C(O)(=O)C.N1CCCCC1>[N+:16]([C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[CH:22]=[C:3]([C:2](=[O:1])[CH3:15])[C:4]([NH:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 74493-NitrobenzaldehydeHCID 54366555t-butyl 2-[N-(3-oxobutanoyl)amino]acetate

Product 1

HCID 53908936t-butyl 2-[N-[2-(3-nitrobenzylidene)-3-oxobutanoyl]amino]acetateYield 85%

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 3776IsopropanolSolvent

Procedure

9.821 g (45.6 mmol) of t-butyl 2-[N-(3-oxobutanoyl)amino]acetate and 6.891 g (45.6 mmol) of 3-nitrobenzaldehyde were suspended in 50 ml of isopropyl alcohol. With addition of 0.331 g (2.28 mmol) of piperidine acetate, the mixture was stirred for 15 hours. The above mixture was ice-cooled for one hour and the precipitated crystals were separated by filtration. The thus obtained crystals were washed with cooled isopropyl alcohol and dried under reduced pressure. The thus obtained crystals were recrystallized from acetonitrile, whereby 13.5 g (85%) of the captioned compound was obtained.

Workup

  1. temperaturecooled for one hour
  2. customthe precipitated crystals were separated by filtration
  3. washThe thus obtained crystals were washed with cooled isopropyl alcohol
  4. customdried under reduced pressure
  5. customThe thus obtained crystals were recrystallized from acetonitrile

Sources & evidence

ORD record
ord-3fe6ab768eae4b9bbfa3d1a361024458
Source dataset
uspto-grants-1999_01
Patent number
US05859244

Reaction notes

Loading…