Stannous Chloride → HCID 66587433, compound

HRID 1630681Notes

Reaction equation

HRID 1630681 reaction equation
[Sn](Cl)Cl.[Cl:4][C:5]1[C:6]([N:11]2[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][C:13]([N+:20]([O-])=O)=[N:12]2)=[N:7][CH:8]=[CH:9][CH:10]=1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:20][C:13]1[CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[N:11]([C:6]2[C:5]([Cl:4])=[CH:10][CH:9]=[CH:8][N:7]=2)[N:12]=1

Participants

5

Reactant 3

HCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 66587477HCID 66587477, compound

Product 1

HCID 66587433HCID 66587433, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.41 g (54.9 mmol) of tin(II) chloride were initially charged in 80 ml of ethanol, 3.20 g (11.3 mmol) of methyl 1-(3-chloropyridin-2-yl)-3-nitro-1H-pyrazole-5-carboxylate were added and the mixture was stirred at reflux temperature for 3 hours. After cooling, the reaction mixture was poured onto ice and adjusted to pH 12 with sodium bicarbonate. The aqueous phase was extracted repeatedly with ethyl acetate and dried over magnesium sulphate. The solvent was distilled off under reduced pressure and the residue was chromatographed on silica gel, which gave 2.20 g (71% of theory) of methyl 3-amino-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylate (log P: 1.09; MH+: 253.1); 1H-NMR (400 MHz, CD3CN, δ, ppm): 3.66 (s, 3H), 5.20 (s, 2H), 6.25 (s, 1H), 7.56 (m, 1H), 8.15 (d, 1H), 8.47 (m, 1H).)

Workup

  1. temperatureat reflux temperature for 3 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured onto ice
  4. extractionThe aqueous phase was extracted repeatedly with ethyl acetate
  5. dry with materialdried over magnesium sulphate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was chromatographed on silica gel, which

Sources & evidence

ORD record
ord-e45d90bf52bc4c7088c37f6daf90b554
Source dataset
uspto-grants-2014_07
Patent number
US08791139B2

Reaction notes

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