Aniline → (E)-Dimethyl 2-(3-(phenylamino)allylidene)malonate

HRID 1670275

Reaktionsgleichung

Reaktionsgleichung von HRID 1670275
[CH3:1][O:2][C:3](=[O:14])[C:4](=[CH:9][CH:10]=[CH:11]OC)[C:5]([O:7][CH3:8])=[O:6].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[C:16]1([NH:15]/[CH:11]=[CH:10]/[CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:14])[C:5]([O:7][CH3:8])=[O:6])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Komponenten

4

Edukt 2

HCID 6115AnilineHCID 5979922-(3-Methoxy-allylidene)-malonic acid dimethyl ester

Produkt 1

HCID 59852887(E)-Dimethyl 2-(3-(phenylamino)allylidene)malonateAusbeute 57,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 2-(3-methoxyallylidene)malonic acid dimethyl ester (Acros Organics, 200 mg, 1.0 mmol) in THF (2 mL) at rt was added aniline (300 mg, 3.2 mmol) and the reaction mixture was heated at 60° C. for 8.5 h. Purification of the reaction mixture by preparative HPLC provided the desired product (150 mg, 57%) as a yellow solid. 1H NMR (DMSO-d6) δ 10.16 (d, 1H, J=12.7 Hz), 8.06 (t, 1H, J=12.7 Hz), 7.74 (d, 1H, J=12.7 Hz), 7.30 (t, 2H, J=8.7 Hz), 7.16 (d, 2H, J=7.7 Hz), 6.98 (t, 1H, J=7.7 Hz), 6.35 (t, 1H, J=12.1 Hz), 3.69 (s, 3H), 3.65 (s, 3H).

Aufarbeitung

  1. customPurification of the reaction mixture by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-13cf9ce188b248e594cebcf89cd29f0d
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989477B2

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