Sodium Hydroxide → HCID 13424153, compound

HRID 1981317Notes

Reaction equation

HRID 1981317 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][CH:10]=2)=[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][C:12]([Cl:15])=[CH:11][CH:10]=2)=[O:8])=[N:5][O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 13424147HCID 13424147, compound

Product 1

HCID 13424153HCID 13424153, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-methyl-4-nitroisoxazol-3-yl)-4-chlorophenylmethanone of Example Va (5.3 g, 20 moles) in tetrahydrofuran (THF) (100 ml) was added to a mixture of SnCl2 2H2O (27 g, 120 mmoles) in concentrated hydrochloric acid (35 ml) and THF (11 ml) 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 3.7 g (78%) of a solid, which was flash chromatographed (20% ethyl acetate:hexane) to yield 2.9 g (62%) of a solid, melting point 84°-86° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with dilute sodium chloride
  3. dry with materialdried (sodium sulfate)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-6ec88a249d24422bbfd36e85f63ed315
Source dataset
uspto-grants-1985_04
Patent number
US04514410

Reaction notes

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