Ethyl Acetoacetate → HCID 23458160, compound

HRID 1679815Notes

Reaction equation

HRID 1679815 reaction equation
[N+]([CH2:4][C:5]([NH:7][C:8]1[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=1)[NH2:11])=[O:6])([O-])=O.[C:15]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:16][C:17]([CH3:19])=O.[H][H]>[Pt].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C>[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:11][CH:17]([CH3:19])[CH2:16][C:15]([O:21][CH2:22][CH3:23])=[O:20])[CH:12]=[CH:13][CH:14]=1)(=[O:6])[CH3:4]

Participants

7

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 54477569HCID 54477569, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23458160HCID 23458160, compoundYield 73.9%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 18.0 g (0.1 mole) of m-nitroacetamido aniline, 26.0 g (0.2 mole) ethyl acetoacetate, 100 ml ethanol, 3.0 g of 5% Pt/C and 0.5 g of p-toluenesulfonic acid is treated in an autoclave at 165° C. and 1,000 psi of hydrogen until the uptake of hydrogen ceases. The solvent and catalyst are removed to yield 19.53 g of ethyl 3-(3'-acetamidophenylamino)butyrate.

Workup

  1. additionis treated in an autoclave at 165° C.
  2. customThe solvent and catalyst are removed

Sources & evidence

ORD record
ord-7d3959c0fe54458daf0c44bc734673d1
Source dataset
uspto-grants-1981_06
Patent number
US04271071

Reaction notes

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