Stannous Chloride → Methyl 3-amino-5-(5-methylpyridin-2-yl)benzoate

HRID 2091813Notes

Reaction equation

HRID 2091813 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:5]=1.Cl[Sn]Cl>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[C:6]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][N:14]=2)[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 578516583-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester

Product 1

HCID 57851018Methyl 3-amino-5-(5-methylpyridin-2-yl)benzoateYield 90%

Reagents, catalysts & solvents 1

HCID 21584119Ethylacetate methanolSolvent

Procedure

To a solution of 3-(5-methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester (4 g, 14.7 mmol) in methanol/ethyl acetate was added SnCl2 (11.15 g, 58.8 mmol) at room temperature. The reaction mixture was refluxed for 3 hours and then cooled. Solvent was removed under reduced pressure and the residue was dissolved in H2O and basified by addition of Na2CO3 to pH=9. The mixture was extracted with CH2Cl2, and the organic phase was washed with water, brine, and dried over Na2SO4. The solvent was removed under reduced pressure to give 3-amino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (3.2 g, 90%) as white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. customSolvent was removed under reduced pressure
  4. dissolutionthe residue was dissolved in H2O
  5. additionbasified by addition of Na2CO3 to pH=9
  6. extractionThe mixture was extracted with CH2Cl2
  7. washthe organic phase was washed with water, brine
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-5fc52467a0684857a868957bc0d5fda1
Source dataset
uspto-grants-2013_05
Patent number
US08440673B2

Reaction notes

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