Reaction #2829

Reaction equation

compound ( [5]-(54)-75 )

4-hexyl-3-nitrobenzoic acid morpholide

hydrazine monohydrate

→

compound ( [5]-(55)-75 )

Yield 99.4%

3-amino-4-hexylbenzoic acid morpholide

Yield 99.4%

Solvents

ethanol

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   Filtrationthe solution was filtered through celite 545
3. 3
   Otherto remove the catalyst
4. 4
   OtherThe solvent was evaporated under reduced pressure
5. 5
   OtherThe residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate)

Procedure

The compound ([5]-(54)-75) (700 mg) prepared in Example 62 was dissolved in ethanol (35 ml). After the solution was heated to 50° C., a suspension of 10% Pd/C (70 mg) in ethanol was added, and hydrazine monohydrate (0.35 ml) was added to the solution. The solution was stirred at 50° C. for 30 minutes. After the reaction was completed, the solution was filtered through celite 545 to remove the catalyst. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (Kieselgel 60=20 g, ethyl acetate) to obtain the above-captioned compound ([5]-(55)-75) (631 mg) as colorless oil.

Source