Sodium Hydroxide → HCID 20265423, compound

HRID 463897Notes

Reaction equation

HRID 463897 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][C:10]=2[F:15])=[O:8])[C:3]=1[N+:16]([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+]>O1CCCC1.Cl>[NH2:16][C:3]1[C:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[F:15])=[O:8])=[N:5][O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 13424148HCID 13424148, compound

Product 1

HCID 20265423HCID 20265423, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-methyl-4-nitroisoxazol-3-yl)-2-fluorophenylmethanone of Example VIa (6.2 g, 25 mmoles) in tetrahydrofuran (THF) (25 ml) was added to a mixture of SnCl2.2H2O (22.4 g, 100 mmoles) in concentrated hydrochloric acid (40 ml) and THF (20 ml) with ice-bath cooling over 1 hour. After warming to room temperature, the reaction mixture was poured into cold 10% sodium hydroxide (500 ml) with stirring and extracted with ethyl acetate. The extracts were washed with dilute sodium chloride and dried (sodium sulfate). Concentration gave an oil which was flash chromatographed (20% ethyl acetate:hexane) to yield 2.4 g (44%) of an oil that solidified.

Workup

  1. temperaturecooling over 1 hour
  2. extractionextracted with ethyl acetate
  3. washThe extracts were washed with dilute sodium chloride
  4. dry with materialdried (sodium sulfate)
  5. concentrationConcentration
  6. customgave an oil which
  7. customchromatographed (20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-b1667019b17348be91aff0616952e8cb
Source dataset
uspto-grants-1985_10
Patent number
US04544753

Reaction notes

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