Sodium Hydroxide → HCID 20265423, compound

HRID 1981320Notes

Reaction equation

HRID 1981320 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.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 24479Stannous ChlorideHCID 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. extractionextracted with ethyl acetate
  2. washThe extracts were washed with dilute sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationConcentration
  5. customgave an oil which
  6. customchromatographed (20% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-aa1a117899b2433d9f4f542f3ee40914
Source dataset
uspto-grants-1985_04
Patent number
US04514410

Reaction notes

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