Stannous Chloride → HCID 57851670, compound

HRID 553768Notes

Reaction equation

HRID 553768 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[C:6]([N:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]2=[O:20])[CH:5]=1.Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:5]=[C:6]([N:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]2=[O:20])[CH:7]=[C:8]([NH2:10])[CH:9]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 578513253-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester

Product 1

HCID 57851670HCID 57851670, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-nitro-benzoic acid methyl ester (1000 mg, 3.47 mmol) in methanol was added SnCl2 (2.63 g, 13.9 mmol) at room temperature. The reaction mixture was refluxed for 3 hours, then cooled to room temperature. Solvent was removed in vacuo, and the residue was dissolved in H2O and basified by addition of Na2CO3 to pH=9. The mixture was extracted with CH2Cl2, and the combined organic phase was washed with water, brine, and dried over Na2SO4. Solvent was removed under vacuum to give 3-Amino-5-(4-Methyl-2-oxo-2H-pyridin-1-yl)benzoic acid methyl ester (895 mg, 100%) as yellow solid. MS (M+H)=260.

Workup

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

Sources & evidence

ORD record
ord-8ff65011e8574cd58e2f6a687be814ac
Source dataset
uspto-grants-2011_11
Patent number
US08048905B2

Reaction notes

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