N-(3-nitrophenyl)-3-oxobutanamide → HCID 68125441, compound

HRID 441268Notes

Reaction equation

HRID 441268 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])([O-:3])=[O:2].[CH:17]([O-])([O-])OC>N1C2C(=CC=CC=2)C=CC=1.C1(C)C=CC=CC=1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[NH:7][C:8](=[O:13])/[CH:9]=[C:10](\[O:12][CH3:17])/[CH3:11])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 296089N-(3-nitrophenyl)-3-oxobutanamideHCID 53629101Methylorthoformate

Product 1

HCID 68125441HCID 68125441, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 7047QuinolineCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 33 g of m-nitro-acetylacetanilide, 38.1 g of methyl orthoformate and 13 drops of 36° Be sulfuric acid was allowed to stand for 16 hours and after the addition of 40 drops of quinoline and 150 ml of toluene, the mixture was heated to 130° C. while distilling of the methanol formed as an azeotrope. The mixture was cooled and vacuum filtered and the recovered precipitate was crystallized from acetone to obtain 24 g of m-nitro-3-methoxy-crotonanilide melting at 187° C.

Workup

  1. distillationwhile distilling of the methanol
  2. customformed as an azeotrope
  3. temperatureThe mixture was cooled
  4. filtrationvacuum filtered
  5. customthe recovered precipitate was crystallized from acetone

Sources & evidence

ORD record
ord-ef43959ebca54ac2b55554b81e9074a3
Source dataset
uspto-grants-1977_08
Patent number
US04039316

Reaction notes

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