Sodium Hydroxide → HCID 13424154, compound

HRID 463899Notes

Reaction equation

HRID 463899 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2[F:16])=[O:8])[C:3]=1[N+:17]([O-])=O.O.O.Cl[Sn]Cl.[OH-].[Na+]>O1CCCC1.Cl>[NH2:17][C:3]1[C:4]([C:7]([C:9]2[C:10]([F:16])=[CH:11][CH:12]=[CH:13][C:14]=2[F:15])=[O:8])=[N:5][O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 13424150HCID 13424150, compound

Product 1

HCID 13424154HCID 13424154, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-methyl-4-nitroisoxazol-3-yl)-2,6-difluorophenylmethanone of Example XIIIb (82.6 g, 308 mmoles) in tetrahydrofuran (THF) (200 ml) was added to a mixture of SnCl2.2H2O (210 g, 938 mmoles) in concentrated hydrochloric acid (400 ml) and THF (400 ml) at 15° C. The reaction mixture was stirred at room temperature for 3 hours and poured into a mixture of 50% sodium hydroxide (700 g) and ice with stirring. The organic phase was separated and the aqueous was extracted with ethyl acetate. The organics were combined, washed with saturated sodium chloride, dried (sodium sulfate), and evaporated to give 63 g of an oil. The residue was flash chromatographed (20% ethyl acetate:hexane) to yield 51 g (70%) of an oil that crystallized on standing. The amine (4.0 g) was chromatographed by high pressure liquid chromatography (20% ethyl acetate:hexane) to yield 2.3 g (40%) of a solid, melting point 63°- 68° C.

Workup

  1. stirringwith stirring
  2. customThe organic phase was separated
  3. extractionthe aqueous was extracted with ethyl acetate
  4. washwashed with saturated sodium chloride
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-4361277023d248ec9fa0ba45c2fec4c8
Source dataset
uspto-grants-1985_10
Patent number
US04544753

Reaction notes

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