Stannous Chloride → HCID 68431840, compound

HRID 2243803Notes

Reaction equation

HRID 2243803 reaction equation
[Cl:1][C:2]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([CH:15]=[CH2:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[Sn]Cl>CCO.O.CCOC(C)=O>[Cl:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([CH:15]=[CH2:16])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

6

Reactant 2

HCID 24479Stannous ChlorideHCID 68433557HCID 68433557, compound

Product 1

HCID 68431840HCID 68431840, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-chloro-3-nitro-5-vinylbenzoate (1.75 g, 7.2 mmol) and SnCl2 (4.1 g, 18.1 mmol) in EtOH (50 mL) was stirred at 75° C. for 16 h. The reaction mixture was cooled to RT, diluted with water and EtOAc, stirred at RT for 10 min, and filtered on cellite. The organic layer was separated, washed with brine, dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography (120 g silica gel, 0 to 25% EtOAc in hexane) to give methyl 2-chloro-3-amino-5-vinylbenzoate as a yellow oil. MS M+1=212.

Workup

  1. filtrationfiltered on cellite
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (120 g silica gel, 0 to 25% EtOAc in hexane)

Sources & evidence

ORD record
ord-2ca549990d0547d3bbf94cd520a2b90f
Source dataset
uspto-grants-2010_03
Patent number
US07678783B2

Reaction notes

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