Tin atom → HCID 18408336, compound

HRID 1385956Notes

Reaction equation

HRID 1385956 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:13]=2[Cl:14])=[CH:4][C:3]=1[N+:21]([O-])=O.[Sn]>C(O)C>[NH2:21][C:3]1[CH:4]=[C:5]([C:8]2[C:9](=[O:20])[N:10]([CH3:19])[C:11]([C:15]([F:18])([F:17])[F:16])=[CH:12][C:13]=2[Cl:14])[CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

4

Reactant 2

HCID 5352426Tin atomHCID 18408320HCID 18408320, compound

Product 1

HCID 18408336HCID 18408336, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

0.5 g (1.37 mmol) of 3-(4-chloro-3-nitrophenyl)-4-chloro-1-methyl-6-trifluoromethyl-2(1H)-pyridone was dissolved in 20 ml of ethanol, and 0.8 g (6.78 mmol) of tin was added thereto with stirring at room temperature, followed by stirring for 1 hour. After completion of the reaction, excess ethanol was distilled off under reduced pressure, and ethyl acetate and a saturated sodium hydrogencarbonate aqueous solution were added. The precipitate was collected by filtration and washed with water and a 10% citric acid aqueous solution. The organic layer was dried over anhydrous magnesium sulfate. The organic layer was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropyl ether to obtain 0.40 g (yield: 87%) of the desired product. 1H-NMR (300 MHz, CDCl3) δ value: 3.74(3H,s), 4.06(2H,s), 6.54(1H,dd), 6.59(1H,s), 6.62(1H,d), 7.27(1H,d)ppm.

Workup

  1. stirringby stirring for 1 hour
  2. distillationwas distilled off under reduced pressure, and ethyl acetate
  3. additiona saturated sodium hydrogencarbonate aqueous solution were added
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationThe organic layer was distilled off under reduced pressure
  8. customthe obtained crude crystals
  9. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-fec41b7e564f44ddb5f1e17648181361
Source dataset
uspto-grants-2001_07
Patent number
US06265349B1

Reaction notes

Loading…