p-Toluenesulfonic acid → Butanoic acid, 3-[[5-(acetylamino)-2-methoxyphenyl]amino]-, ethyl ester

HRID 2166856

Reaction equation

HRID 2166856 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([NH:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[O:14][CH3:15])([O-])=O.[C:16]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:17][C:18]([CH3:20])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>[Pt].C(O)(C)C>[CH3:15][O:14][C:5]1[CH:6]=[CH:7][C:8]([NH:10][C:11](=[O:13])[CH3:12])=[CH:9][C:4]=1[NH:1][CH:18]([CH3:20])[CH2:17][C:16]([O:22][CH2:23][CH3:24])=[O:21]

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8868Ethyl AcetoacetateHCID 950434'-Methoxy-3'-nitroacetanilideHCID 178418361HCID 178418361, compound2×

Product 1

HCID 172818Butanoic acid, 3-[[5-(acetylamino)-2-methoxyphenyl]amino]-, ethyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 105.0 g. (0.5 mole) of 2-nitro-4-acetamidoanisole, 67.0 g. (0.5 mole) of ethyl acetoacetate, 550 ml. of isopropyl alcohol, 10.0 g. of 5% Pt/C, and 3.0 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 catalysts are removed. Upon standing, 143.8 g. (98%) of ethyl 3-(2'-methoxy-5-acetamidoanilino)butyrate is obtained. NMR analysis of the product supports the proposed structure.

Workup

  1. additionA mixture of 105.0 g
  2. customThe solvent and catalysts are removed

Sources & evidence

ORD record
ord-451eded8c84b4688af791421495fb604
Source dataset
uspto-grants-1983_06
Patent number
US04389531

Linked notes

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