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

HRID 2380426Notes

Reaction equation

HRID 2380426 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-3ca66ff0a1344173bafb679e85ef2e77
Source dataset
uspto-grants-1994_11
Patent number
US05367081

Reaction notes

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