Stannous Chloride → Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

HRID 1888896Notes

Reaction equation

HRID 1888896 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:8]=[C:9]([N+:11]([O-])=O)[CH:10]=1)=[O:4].Cl[Sn]Cl>CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[CH:8]=[C:9]([NH2:11])[CH:10]=1)=[O:4]

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 57851213Methyl 3-(4-methylphenyl)-5-nitrobenzoate

Product 1

HCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylateYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4′-Methyl-5-nitro-biphenyl-3-carboxylic acid methyl ester (10.00 g, 36.9 mmol) in methanol was added SnCl2 (27.98 g, 147.6 mmol) at room temperature. The reaction mixture was refluxed for 3 hours, then cooled. Solvent was removed in vacuo and the residue was dissolved in H2O, then basified by addition of Na2CO3 to pH=9. The mixture was extracted by CH2Cl2, and the organic phase was washed with water followed by brine, and dried over Na2SO4. The solvent was removed under vacuum to give 5-amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (8.48 g, 95%) as yellow oil. MS (M+H)=242.

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. additionbasified by addition of Na2CO3 to pH=9
  6. extractionThe mixture was extracted by CH2Cl2
  7. washthe organic phase was washed with water
  8. dry with materialdried over Na2SO4
  9. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-a0ea548cbdc8456c9483be1bdcc19ab8
Source dataset
uspto-grants-2013_08
Patent number
US08501933B2

Reaction notes

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