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

HRID 217326Notes

Reaction equation

HRID 217326 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>[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 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(5-Methyl-pyridin-2-yl)-5-nitro-benzoic acid methyl ester (410 mg, 36.9 mmol) in methanol was added SnCl2 (1.36 g, 6.03 mmol) at room temperature. The reaction mixture was refluxed for 3 hours and then cooled. Solvent was removed in vacuo and the residue was dissolved in H2O and basified by 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 vacuum to give 3-amino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (362 m g, 100%) as yellow oil. MS (M+H)=244.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. temperaturecooled
  3. customSolvent was removed in vacuo
  4. dissolutionthe residue was dissolved in H2O
  5. extractionThe mixture was extracted with CH2Cl2
  6. washthe organic phase was washed with water, brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e983d14b6f7d420ab2e06258e3095b9d
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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