Reaction #82439

Reaction equation

beta-alanine

2,4-dinitrofluorobenzene

→

solid

Yield 77.0%

3-(2',4'-Dinitrophenylamino) propionic acid

Yield 77.0%

Solvents

NaHCO3

ethanol

Conditions

Workup

1. 1
   Otherevaporated
2. 2
   Otherto remove the volatile in vacuo
3. 3
   OtherThe residue was transferred to a separatory funnel with water
4. 4
   Washwashed twice with ethyl ether
5. 5
   OtherThe aqueous layer was acidified with 1N HCl until precipitation
6. 6
   FiltrationThe mixture was filtered
7. 7
   Washthe wet cake washed with ether
8. 8
   workup.DISSOLUTIONfrom dissolving the solid in 1M NaHCO3
9. 9
   Washwashing the ether
10. 10
    Otherprecipitating with 1N HCl

Procedure

To a solution of beta-alanine (1.0 g, 11.1 mmole) in 50 ml of 1M NaHCO3 was added 2,4-dinitrofluorobenzene (10.4 g, 56 mmole) in 100 ml of ethanol. The reaction mixture was stirred at room temperature for 2 hours and evaporated to remove the volatile in vacuo. The residue was transferred to a separatory funnel with water and washed twice with ethyl ether. The aqueous layer was acidified with 1N HCl until precipitation was complete. The mixture was filtered and the wet cake washed with ether. This purification process, starting from dissolving the solid in 1M NaHCO3, washing the ether, and precipitating with 1N HCl, was repeated in the same manner to give yellow solid (1.6 g, 77%). e(MeOH)=7900 (260 nm), 15900 (350 nm). NMR spectral analysis was consistent with the structure.

Source