2-Methoxyaniline → HCID 23458158, compound

HRID 1679816Notes

Reaction equation

HRID 1679816 reaction equation
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][C:13](=[O:18])[CH2:14][C:15]([CH3:17])=O)[CH3:11].[H][H]>[Pt].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][CH:15]([CH3:17])[CH2:14][C:13]([O:12][CH2:10][CH3:11])=[O:18]

Participants

7

Reactant 3

HCID 70002-MethoxyanilineHCID 8868Ethyl AcetoacetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 23458158HCID 23458158, compoundYield 62.8%

Reagents, catalysts & solvents 3

HCID 6101p-Toluenesulfonic acidCatalystHCID 23939PlatinumCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of 123.0 g (1 mole) of o-anisidine, 260.0 g (2 moles) of ethylacetoacetate, 400 ml of isopropyl alcohol, 10.0 g of 1% Pt/C, 2.5 g of p-toluenesulfonic acid is treated in an autoclave at 165° C., with 1000 psi of hydrogen until the uptake of hydrogen ceases. The catalyst is removed by filtration. The solution is distilled under vacuum to yield 149.0 g of ethyl 3(2'-methoxyphenylamino)butyrate.

Workup

  1. customThe catalyst is removed by filtration
  2. distillationThe solution is distilled under vacuum

Sources & evidence

ORD record
ord-098e62d128ac49ee867b4ab84c08c89e
Source dataset
uspto-grants-1981_06
Patent number
US04271071

Reaction notes

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