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

HRID 2278717Notes

Reaction equation

HRID 2278717 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([N+:14]([O-])=O)[CH:11]=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:9]=2)=[CH:4][CH:3]=1.[Sn](Cl)Cl>CO>[NH2:14][C:12]1[CH:11]=[C:10]([C:17]([O:19][CH3:20])=[O:18])[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)[CH:13]=1

Participants

4

Reactant 2

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

Product 1

HCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution methyl 4′-methyl-5-nitrobiphenyl-3-carboxylate (4.58 g, 16 mmol) in methanol (130 mL) was added tin dichloride (12.56 g, 64.2 mmol) at room temperature. The mixture was heated under reflux for 3 hours. After cooling, the mixture was concentrated in vacuo. The residue was treated with water, basified to pH=9 by addition of Na2CO3, and extracted with CH2Cl2. The organic layer was dried over MgSO4, filtered and concentrated to afford a white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated in vacuo
  5. additionThe residue was treated with water
  6. additionbasified to pH=9 by addition of Na2CO3
  7. extractionextracted with CH2Cl2
  8. dry with materialThe organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford a white solid

Sources & evidence

ORD record
ord-32152c0ed3e347fd82ed7144c07ab281
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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