Stannous Chloride → HCID 12897332, compound

HRID 852535Notes

Reaction equation

HRID 852535 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([Cl:13])=[C:6]([N+:14]([O-])=O)[CH:5]=1.Cl[Sn]Cl>CO>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([Cl:13])=[C:6]([NH2:14])[CH:5]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 96161Methyl 4-chloro-3,5-dinitrobenzoate

Product 1

HCID 12897332HCID 12897332, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-chloro-3,5-dinitro-benzoic acid methyl ester (D25a) (2.6 g, 10 mmol, 1 equiv) and SnCl2 (18.95 g, 100 mmol, 10 equiv) in MeOH (80 ml) was refluxed for 1 h, cooled to room temperature and concentrated in vacuo. The residue was partitioned between AcOEt and 2N aqueous NaOH solution. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was triturated with 1:1 Et2O/iso-hexane to give 3,5-diamino-4-chloro-benzoic acid methyl ester (D27a) (1.56 g, 78%) as a light orange solid.

Workup

  1. temperaturewas refluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between AcOEt and 2N aqueous NaOH solution
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was triturated with 1:1 Et2O/iso-hexane

Sources & evidence

ORD record
ord-2c7e24dbe53d46148841c76a71afd65b
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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