Ethyl Acetoacetate → HCID 178428848, compound

HRID 408653Notes

Reaction equation

HRID 408653 reaction equation
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9](OCC)(=[O:14])[CH2:10][C:11]([CH3:13])=O>O1CCOCC1.O.C(=O)([O-])[O-].[Na+].[Na+]>[OH:14][C:9]1[C:7]2[C:5](=[CH:4][CH:3]=[C:2]([I:1])[CH:8]=2)[N:6]=[C:11]([CH3:13])[CH:10]=1

Participants

6

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 108934-Iodoaniline

Product 1

HCID 178428848HCID 178428848, compoundYield 30.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Iodoaniline (25 g), ethyl acetoacetate (17.8 g) and polyphosphoric acid (112.5 g) in dioxane (500 mL) were refluxed for 20 hours. The reaction was diluted with water (2 L) and solid sodium carbonate added until the solution reached pH 10.0. The resulting precipitate was isolated by filtration, washed with water and dried under vacuum. Trituration with ether gave the sub-title compound (10 g) as a white solid.

Workup

  1. additionadded until the solution
  2. customThe resulting precipitate was isolated by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-b3a92f4c77e24107843e2a5a49a75f92
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

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