Hydrazine hydrate (1:1) → C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamine

HRID 1807543Notes

Reaction equation

HRID 1807543 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[C:8]([CH3:22])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4].O.NN>CO>[CH2:1]([C:5]1[C:9]([CH2:10][NH2:11])=[C:8]([CH3:22])[O:7][N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 666459502-(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 66643513C-(3-Butyl-5-methyl-isoxazol-4-yl)-methylamineYield 81.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

2-(3-Butyl-5-methyl-isoxazol-4-ylmethyl)-isoindole-1,3-dione (1.20 g, 4.0 mmol) was dissolved in MeOH (20 mL) then hydrazine hydrate (1.51 g, 30.1 mmol) was added and the reaction mixture heated at 55° C. After 2 h the reaction mixture was cooled and filtered. The filtrate was evaporated then purified by chromatography (silica, 2 to 10% methanol in dichloromethane) to give the title compound (550 mg, 81%) as a yellow liquid. MS: m/e=348.5 [M+H]+.

Workup

  1. temperatureAfter 2 h the reaction mixture was cooled
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthen purified by chromatography (silica, 2 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-dc1f29912159410ea98cef977d906740
Source dataset
uspto-grants-2013_01
Patent number
US08357703B2

Reaction notes

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