Thionyl Chloride → Methyl 5-amino-2-nitrobenzoate

HRID 1094991Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094991
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH2:14](OC(=O)C1C=C(N2CCCCC2)C=CC=1N)C.S(Cl)(Cl)=O>CO>[CH3:14][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([NH2:1])[CH:3]=[CH:4][C:5]=1[N+:11]([O-:13])=[O:12]

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 832985-Amino-2-nitrobenzoic acidHCID 613065672-Amino-5-piperidin-1-yl-benzoic acid ethyl ester

Produkt 1

HCID 11446896Methyl 5-amino-2-nitrobenzoateAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

5-Amino-2-nitro-benzoic acid (compound A′) (910 mg) was dissolved in methanol (50 ml). Thionyl chloride (0.74 ml) was added dropwise to the solution on an ice bath, and a reaction was allowed to proceed under reflux with heating for 12 hr. After the completion of the reaction, the reaction solution was allowed to stand for cooling to room temperature and was then concentrated under the reduced pressure. The residue was purified by column chromatography eluted with a chloroform-methanol system to give 5-amino-2-nitro-benzoic acid methyl ester (410 mg, yield 42%).

Aufarbeitung

  1. temperatureunder reflux
  2. temperaturewith heating for 12 hr
  3. customAfter the completion of the reaction
  4. concentrationwas then concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluted with a chloroform-methanol system

Quellen und Nachweise

ORD-Eintrag
ord-4bd5328ed55747c48fbafa16bc0bea07
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134015B2

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