Dimethylamine → (3-Dimethylamino-4-nitrophenyl)acetic acid methyl ester

HRID 494394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494394
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7](Br)[CH:6]=1.[CH2:16]([N:18](CC)[CH2:19]C)C.CNC>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7]([N:18]([CH3:19])[CH3:16])[CH:6]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 8471TriethylamineHCID 23512304Methyl (3-bromo-4-nitrophenyl)acetate

Produkt 1

HCID 57683228(3-Dimethylamino-4-nitrophenyl)acetic acid methyl esterAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The (3-bromo-4-nitrophenyl)acetic acid methyl ester (0.320 g) obtained in Example 4 b) was dissolved in tetrahydrofuran (10 mL). To this solution were added triethylamine (0.237 g) and dimethylamine (2M tetrahydrofuran; 0.58 mL), and stirred overnight while heating. The reaction mixture was concentrated and purified by column chromatography on silica gel with ethyl acetate:hexane=1:4 to give the title compound (0.145 g) as an orange oil.

Aufarbeitung

  1. temperaturewhile heating
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography on silica gel with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-efbeafdebaa5485da110576852eea2c9
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538140B2

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