Sodium Hydroxide → HCID 13424152, compound

HRID 1981315Notes

Reaction equation

HRID 1981315 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[Cl: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[Cl:15])=[O:8])=[N:5][O:6][C:2]=1[CH3:1]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 20265446HCID 20265446, compound

Product 1

HCID 13424152HCID 13424152, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (5-methyl-4-nitroisoxazol-3-yl)-2-chlorophenylmethanone of Example IIIa (5.3 g, 20 mmoles) in tetrahydrofuran (THF) (25 ml) was added to a mixture of SnCl2 2H2O (18 g, 80 mmoles) in concentrated hydrochloric acid (35 ml) and THF (20 ml) over 1 hour. After stirring overnight at room temperature (about 16 hours), 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 3.0 g (64%) of an oil that solidified. The resultant amine was triturated with cyclohexane (40 ml) to yield 2.4 g (51%) of a powder, melting point 75°-78° C.

Workup

  1. stirringwith stirring
  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-d2e44eb172b84a16b5d4d8281bf871de
Source dataset
uspto-grants-1985_04
Patent number
US04514410

Reaction notes

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