Potassium Carbonate → HCID 57503083, compound

HRID 2353571Notes

Reaction equation

HRID 2353571 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[C:5]([N+:16]([O-])=O)=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.C([O-])([O-])=O.[K+].[K+]>Cl.C(OCC)(=O)C>[NH2:16][C:5]1[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 61436Stannous chloride dihydrateHCID 43330303HCID 43330303, compound

Product 1

HCID 57503083HCID 57503083, compoundYield 102.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 6-chloro-3-nitro-pyridin-2-yl-p-tolyl-amine (527 mg, 2 mmol) and tin(II) chloride dihydrate (2.72 g, 12 mmol) in 4 mL conc. HCl was heated at 90° C. for 2 h. After cooling down the yellow suspension was diluted with ethyl acetate and treated with aq. K2CO3 at 0° C. under vigorous stirring to pH 10. The emulsion was extracted with 5×30 mL EtOAc. The combined organic phase was dried over Na2SO4. Evaporation gave 479 mg (yield: quantitative) of the title compound, which was pure by LC-MS and used for further reaction without any purification. Calculated mass=233. Observed mass=234.

Workup

  1. temperatureAfter cooling down the yellow suspension
  2. extractionThe emulsion was extracted with 5×30 mL EtOAc
  3. dry with materialThe combined organic phase was dried over Na2SO4
  4. customEvaporation

Sources & evidence

ORD record
ord-ad68aa2571c844548bf7a18f6bfd833f
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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