Sodium Hydroxide → 5-Amino-2-chloro-N-methylbenzamide

HRID 1591615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1591615
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].[Sn](Cl)Cl.[OH-].[Na+]>Cl>[NH2:12][C:9]1[CH:10]=[CH:11][C:2]([Cl:1])=[C:3]([CH:8]=1)[C:4]([NH:6][CH3:7])=[O:5]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 27951452-chloro-N-methyl-5-nitrobenzamide

Produkt 1

HCID 167723205-Amino-2-chloro-N-methylbenzamideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel2×

Versuchsvorschrift

To a suspension of 2-chloro-N-methyl-5-nitro-benzamide (2.3 mmol) in concentrated hydrochloric acid (3 ml) was added a solution of tin dichloride (1.4 g, 7.2 mmol) in concentrated hydrochloric acid (4 ml). After stirring for 20 hours, the mixture was cooled in an ice bath and treated with 50% sodium hydroxide to basic pH. The mixture was extracted with ethyl acetate (3×25 ml). The combined extracts were dried over sodium sulfate and concentrated under reduced pressure to provide 5-amino-2-chloro-N-methylbenzamide (274 mg, 88% yield).

Aufarbeitung

  1. temperaturethe mixture was cooled in an ice bath
  2. extractionThe mixture was extracted with ethyl acetate (3×25 ml)
  3. dry with materialThe combined extracts were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-874ef4e3c92b4d5f8d930fddd42a1b34
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291616B2

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