Sodium Hydroxide → HCID 13424151, compound

HRID 463891Notes

Reaction equation

HRID 463891 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])[C:3]=1[N+:15]([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+]>C(O)(=O)C.Cl>[NH2:15][C:3]1[C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:8])=[N:5][O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 13424146HCID 13424146, compound

Product 1

HCID 13424151HCID 13424151, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 47 g (0.20 mole)(5-methyl-4-nitroisoxazol-3-yl)phenylmethanone of Example Ia in 600 ml glacial acetic acid was added to a mixture of 360 g (1.60 moles) SnCl2.2H2O in one liter of concentrated hydrochloric acid and 200 ml acetic acid at room temperature. After stirring at room temperature overnight (about 16 hours), the reaction mixture was poured carefully into a well stirred mixture of 2400 g of 50% sodium hydroxide and 6500 ml ice with ice bath cooling. The resulting solids were collected by filtration, washed with water and partitioned between 600 ml 5% sodium hydroxide and 2 liters of 1:1 dichloromethane:diethyl ether. The aqueous was extracted thrice with diethyl ether and the organic extract was dried (magnesium sulfate). Concentration gave 26.3 g (65%) of an oil. Chromatography on high pressure liquid chromatograph (HPLC) using dicloromethane as an eluent of 4.0 g of this oil yielded 2.7 g (44%) of an oil that solidified on standing.

Workup

  1. additionthe reaction mixture was poured carefully into a well
  2. stirringstirred
  3. temperaturecooling
  4. filtrationThe resulting solids were collected by filtration
  5. washwashed with water
  6. custompartitioned between 600 ml 5% sodium hydroxide and 2 liters of 1:1 dichloromethane
  7. extractionThe aqueous was extracted thrice with diethyl ether
  8. extractionthe organic extract
  9. dry with materialwas dried (magnesium sulfate)
  10. concentrationConcentration

Sources & evidence

ORD record
ord-6ed066b468bc485690cba791be79e778
Source dataset
uspto-grants-1985_10
Patent number
US04544753

Reaction notes

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