Methanol → Methyl 3-amino-3-(3-nitrophenyl)propanoate

HRID 578617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 578617
[NH2:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].S(Cl)(Cl)=O.[CH3:20]O>>[CH3:20][O:5][C:4](=[O:6])[CH2:3][CH:2]([NH2:1])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2373203-Amino-3-(3-nitrophenyl)propanoic acid

Produkt 1

HCID 2769472Methyl 3-amino-3-(3-nitrophenyl)propanoate

Versuchsvorschrift

To a solution of 3-amino-3-(3-nitrophenyl)propanoic acid (20.00 g; 95.15 mmol; 1.00 eq.) in MeOH (300 mL) was added thionyl chloride (50.00 ml; 761.22 mmol; 8.00 eq.) at 0° C. slowly. Then the mixture was warmed to room temperature and stirred overnight. The reaction mixture was evaporated and the crude product was purified by flash chromatography on silica gel (MeOH: DCM=15:85) to obtain 20 g of the title compound. LCMS [225 (M+1)].

Aufarbeitung

  1. customThe reaction mixture was evaporated
  2. customthe crude product was purified by flash chromatography on silica gel (MeOH: DCM=15:85)

Quellen und Nachweise

ORD-Eintrag
ord-3d7a2701c3c04277a88fd59e16a049f2
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040560B2

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