Aniline → Diethyl 2-butyl-3-(phenylamino)-2-butenedioate

HRID 1110112Notes

Reaction equation

HRID 1110112 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([CH:12]([C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:10][CH3:11]>>[CH2:8]([C:12](=[C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 6115AnilineHCID 251159Diethyl 2-butyl-3-oxobutanedioate

Product 1

HCID 67576867Diethyl 2-butyl-3-(phenylamino)-2-butenedioateYield 45.2%

Conditions

Temperature
75 °C

Procedure

A mixture of 1 g of aniline and 2.65 g of the product of Step A and 150 mg of siliporite® NK10 was stirred for 3 days at 75° C. and the reaction mixture was cooled and chromatographed on silica eluant: hexane - ethyl acetate (9-1) to obtain 1.55 g of the expected product.

Workup

  1. temperaturethe reaction mixture was cooled
  2. customchromatographed on silica eluant

Sources & evidence

ORD record
ord-c88e5a59c26a4df9b7400e8ffa2216a1
Source dataset
uspto-grants-1994_06
Patent number
US05324839

Reaction notes

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