Hydrazine hydrate (1:1) → C-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methylamine

HRID 83296Notes

Reaction equation

HRID 83296 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([CH2:13][N:14]3C(=O)C4C(=CC=CC=4)C3=O)=[C:11]([CH3:25])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.O.NN>C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([CH2:13][NH2:14])=[C:11]([CH3:25])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 671575752-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione

Product 1

HCID 67157896C-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methylamineYield 77%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione (6.3 g, 19 mmol) in THF (252 mL) and ethanol (22 mL) at 0° C. was added hydrazine hydrate (7.0 g, 6.8 mL, 140 mmol) and the resulting mixture stirred at room temperature overnight. The mixture was then filtered and the filtrate diluted with HCl (1 N) and extracted with ethyl acetate. The combined organic extracts were then washed with HCl (1 N) and the aqueous layer made basic with NaOH (6 N). The aqueous layers were extracted with ethyl acetate and the combined organic layers washed with brine and dried over sodium sulfate. Concentration and purification by chromatography (NH2—SiO2, dichloromethane) afforded the title compound (3.0 g, 77%) as a yellow oil. MS: m/e=207.3 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. additionthe filtrate diluted with HCl (1 N)
  3. extractionextracted with ethyl acetate
  4. washThe combined organic extracts were then washed with HCl (1 N)
  5. extractionThe aqueous layers were extracted with ethyl acetate
  6. washthe combined organic layers washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration and purification by chromatography (NH2—SiO2, dichloromethane)

Sources & evidence

ORD record
ord-bb158d8e24994536b1ffea23236605b4
Source dataset
uspto-grants-2014_09
Patent number
US08846719B2

Reaction notes

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