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

HRID 263716Notes

Reaction equation

HRID 263716 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)(=O)C.N1CCCCC1>C(O)(C)C>[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 3

HCID 74493-NitrobenzaldehydeHCID 9793820Piperidine, acetateHCID 54366555t-butyl 2-[N-(3-oxobutanoyl)amino]acetate

Product 1

HCID 53908936t-butyl 2-[N-[2-(3-nitrobenzylidene)-3-oxobutanoyl]amino]acetate

Reagents, catalysts & solvents 1

HCID 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 obtianed.

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, whereby 13.5 g (85%) of the captioned compound

Sources & evidence

ORD record
ord-774ce944ef61408690887af9dcf1fa1d
Source dataset
uspto-grants-1997_07
Patent number
US05644059

Reaction notes

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