Ethyl Acetoacetate → 3-(4-Ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl ester

HRID 2301325Notes

Reaction equation

HRID 2301325 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([I:13])[CH:7]=1)[CH3:2].[C:15]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:16][C:17]([CH3:19])=O>C1C=CC=CC=1.O.C1(C)C(S(O)(=O)=O)=CC=CC=1>[CH2:22]([O:21][C:15](=[O:20])[CH:16]=[C:17]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])=[CH:7][C:8]=1[I:13])[CH3:19])[CH3:23]

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 18372435Ethyl 2-(4-amino-3-iodophenyl)acetate

Product 1

HCID 701032823-(4-Ethoxycarbonylmethyl-2-iodo-phenylamino)but-2-enoic acid ethyl esterYield 93%

Reagents, catalysts & solvents 2

HCID 124969952-Methylbenzenesulfonic acid hydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of (4-amino-3-iodo-phenyl)acetic acid ethyl ester (9.85 g, 32.3 mmol), ethyl acetoacetate (4.2 g, 32.3 mmol), and toluenesulfonic acid monohydrate (0.3 g, 1.6 mmol) in benzene (150 mL) is refluxed under Dean-Stark conditions overnight. The solution is then cooled to room temperature and washed with sodium bicarbonate (NaHCO3) (2×50 mL) and concentrated in vacuo to give the desired product (12.5 g, 93%). The product is used without further purification in Step 3. MS: 418 (M+1)+.

Workup

  1. washwashed with sodium bicarbonate (NaHCO3) (2×50 mL)
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30941cdec4d14235b5b023d695f204f5
Source dataset
uspto-grants-2002_12
Patent number
US06500837B2

Reaction notes

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