Methyl 4-aminobenzoate → Diethyl 2-butyl-3-[(4-(methoxycarbonyl)-phenyl)-amino]-2-butenedioate

HRID 1602946Notes

Reaction equation

HRID 1602946 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[CH2:12]([CH:16]([C:22](=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:14][CH3:15]>CCCCCC.C(OCC)(=O)C>[CH2:12]([C:16](=[C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][CH:11]=1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 251159Diethyl 2-butyl-3-oxobutanedioate

Product 1

HCID 67577966Diethyl 2-butyl-3-[(4-(methoxycarbonyl)-phenyl)-amino]-2-butenedioateYield 100.8%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
60 °C

Procedure

27.8 g of methyl 4-aminobenzoate and 47 g of diethyl 2-butyl-3-oxo-butanedioate were mixed and 2 g of activated siliporite were added. The mixture was stirred for about 30 hours at 60° C. and after chromatography (eluant: hexane-ethyl acetate 95-5), 70 g of the expected product were obtained.

Workup

  1. addition2 g of activated siliporite were added

Sources & evidence

ORD record
ord-bf78c89fb387424f95711f87e8397512
Source dataset
uspto-grants-1999_11
Patent number
US05985894

Reaction notes

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