Acetone → 4'-Nitroacetoacetanilide

HRID 1491659Notes

Reaction equation

HRID 1491659 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([O-:3])=[O:2].CC1(C)[O:17][C:16](=O)[CH:15]=[C:14]([CH3:19])[O:13]1.CC(C)=O>C1(C)C(C)=CC=CC=1>[N+:1]([C:4]1[CH:10]=[CH:9][C:7]([NH:8][C:16](=[O:17])[CH2:15][C:14](=[O:13])[CH3:19])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 74754-NitroanilineHCID 793682,2,6-Trimethyl-4H-1,3-dioxin-4-one

Product 1

HCID 785474'-NitroacetoacetanilideYield 52.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

13.8 g (0.1 mol) of 4-nitroaniline were suspended in 20 ml of dry xylene and 14,22 g (0.1 mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one were added. The reaction mixture was heated in an oil-bath at 150° C. for 30 minutes while the acetone formed in the reaction was removed by distillation. The reaction mixture was cooled to room temperature, filtered and the residue was washed thoroughly with ethyl acetate. The filtrate was evaporated to obtain 11.65 g (52%) of N-(4-nitrophenyl)-3-oxobutanamide as a white crystalline solid melting at 119°-21° C. (from ethyl acetate-petroleum ether (40°-60° C.)) (lit.* melting at 120°-122° C.).

Workup

  1. customformed in the reaction
  2. customwas removed by distillation
  3. filtrationfiltered
  4. washthe residue was washed thoroughly with ethyl acetate
  5. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-de83f6ed55ff4fbf98d4b03f7a86cfb9
Source dataset
uspto-grants-1994_12
Patent number
US05371099

Reaction notes

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