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

HRID 548880Notes

Reaction equation

HRID 548880 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.O.NN>C1COCC1.C(O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:12]([CH2:13][NH2:14])=[C:11]([CH3:25])[O:10][N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 671580562-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione

Product 1

HCID 28750529C-[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methylamineYield 54%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-isoindole-1,3-dione (5.9 g, 18 mmol) in THF (248 mL) and ethanol (21 mL) at 0° C. was added hydrazine hydrate (6.7 g, 6.5 mL, 134 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 afforded the title compound (2.0 g, 54%) as a light yellow oil. MS: m/e=190.3 [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

Sources & evidence

ORD record
ord-7936ef739cfb43f58546892ff074aca3
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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