Stannous Chloride → HCID 21696672, compound

HRID 378783Notes

Reaction equation

HRID 378783 reaction equation
[Cl:1][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[N:4][C:5]([Cl:13])=[C:6]([O:11][CH3:12])[C:7]=1[N+:8]([O-])=O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:8][C:7]1[C:6]([O:11][CH3:12])=[C:5]([Cl:13])[N:4]=[C:3]([C:14]([O:16][CH3:17])=[O:15])[C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 21696607HCID 21696607, compound

Product 1

HCID 21696672HCID 21696672, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To methyl 3,6-dichloro-5-methoxy-4-nitropyridine-2-carboxylate (0.300 g, 1.06 mmol) in 5 mL of ethyl acetate was added SnCl2×2H2O (1.60 g, 7.1 mmol). The reaction mixture was heated to 70° C. for 30 min and then cooled to room temperature. Saturated sodium bicarbonate and a saturated solution of KHF2 were added to reaction mixture. The mixture was extracted with ethyl acetate and the layers were separated. The aqueous layer was washed 2 more times with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated to dryness to give 0.250 g of a yellow solid.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. customthe layers were separated
  4. washThe aqueous layer was washed 2 more times with ethyl acetate
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-40e392f7ca3f40bb82713648f875e44a
Source dataset
uspto-grants-2001_10
Patent number
US06297197B1

Reaction notes

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