Sodium Carbonate → Methyl 3-amino-2-chlorobenzoate

HRID 51345

Reaktionsgleichung

Reaktionsgleichung von HRID 51345
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[Na+].[Na+].[Cl:15][C:16]1[C:25]([N+:26]([O-])=O)=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]>O.CO.O1CCCC1>[Cl:15][C:16]1[C:25]([NH2:26])=[CH:24][CH:23]=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19]

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 24489Sodium DithioniteHCID 10751184Methyl 2-chloro-3-nitrobenzoate

Produkt 1

HCID 15132848Methyl 3-amino-2-chlorobenzoateAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of sodium dithionite (14.0 g, 20.0 mM) and sodium carbonate (6.7 g) in 200 mL of water was slowly added to a solution of methyl 2-chloro-3-nitrobenzoate (6.0 g, 27.9 mM) in 40 mL methanol and 40 mL of tetrahydrofuran at 25° C. over 30 minutes. The mixture was stirred at room temperature for an additional 30 minutes, then extracted with ethyl acetate. The extracts were washed with brine, dried over sodium sulfate, filtered and concentrated to afford 1.2 g (33%) of methyl 2-chloro-3-aminobenzoate as a yellow oil, identical in all respects to the material derived via catalytic hydrogenation described above.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-30ba62e1d7874851b08419fdc0f3fa6a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713645B1

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