Acetic Acid → Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoate

HRID 845033Notes

Reaction equation

HRID 845033 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([O:18][CH3:19])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C(O)(=O)C.N1CCCCC1>O.C1C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:13]([C:14](=[O:15])[CH3:16])[C:12]([O:18][CH3:19])=[O:17])[CH:9]=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 74493-NitrobenzaldehydeHCID 7757Methyl acetoacetateHCID 8082Piperidine

Product 1

HCID 1536427Methyl 2-((3-nitrophenyl)methylene)-3-oxobutanoateYield 72.2%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A solution of 151 g (1.00 mole) of 3-nitrobenzaldehyde, 116 g (1.00 mole) of methyl acetoacetate, 10 mL of glacial acetic acid, 4 mL of piperidine, and 400 mL of benzene was refluxed 2 hr during which time 21 mL of water was removed via a Dean-Stark trap. The dark yellow solution was cooled to ambient temperature and solidification occurred. Filtration followed by washing with ether afforded 180 g of product as a yellow solid. An additional 23 g product was obtained from the filtrate to yield a total of 203 g (82%) of product, m.p. 145°-146° C. (literature m.p., 158° C.; cf: Meyer, et al., Arzneim.- Forsch/Drug Research, 31, 407 (1981)).

Workup

  1. customwas removed via a Dean-Stark trap
  2. filtrationFiltration
  3. washby washing with ether

Sources & evidence

ORD record
ord-24462752d54e4989b966118620c5c925
Source dataset
uspto-grants-1988_07
Patent number
US04755512

Reaction notes

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