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

HRID 963676Notes

Reaction equation

HRID 963676 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-9086b7ee8d2b4136b91af18fb2eda230
Source dataset
uspto-grants-1998_06
Patent number
US05763614

Reaction notes

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