Thionyl Chloride → Methyl 5-amino-2-nitrobenzoate

HRID 1094991Notes

Reaction equation

HRID 1094991 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-4bd5328ed55747c48fbafa16bc0bea07
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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