Reaktion #216698

Reaktionsgleichung

4-Nitrobenzeneacetic acid

THF

carbonyldiimidazole

Carbon dioxide

→

product ( 6 )

Ausbeute 66.6%

N-Methyl-1H-indole-5-acetamide

Ausbeute 66.6%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeGaseous methylamine was then bubbled through the mixture until it
2. 2
   SonstigeThe THF was removed in vacuo and water (70 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   FiltrationThe solid material was collected by filtration
5. 5
   workup.ADDITIONA solution of EtOH (200 mL) and 1N HCl (50 mL) was added
6. 6
   workup.WAITthe mixture was hydrogenated at 60 psi for 4 h
7. 7
   FiltrationThe reaction was filtered
8. 8
   Einengenconcentrated in vacuo
9. 9
   ExtraktionThe aqueous mixture was extracted with EtOAc
10. 10
    WaschenThe combined organic layers were washed with brine
11. 11
    Trocknendried over MgSO4
12. 12
    Filtrationfiltered
13. 13
    Einengenconcentrated in vacuo

Vorschrift

4-Nitrobenzeneacetic acid (16.6 g, 0.0916 mol) was dissolved in THF (200 mL) and carbonyldiimidazole (CDI, 15.6 g, 0.0963 mol) was added. Carbon dioxide evolution rapidly ensued and the reaction mixture was stirred at RT for 30 min. Gaseous methylamine was then bubbled through the mixture until it was distinctly basic to litmus paper. The THF was removed in vacuo and water (70 mL) was added. The solid material was collected by filtration and placed in a Parr bottle were palladium on carbon (10%, 3 g). A solution of EtOH (200 mL) and 1N HCl (50 mL) was added and the mixture was hydrogenated at 60 psi for 4 h. The reaction was filtered, concentrated in vacuo and the residue made basic with saturated aqueous Na2CO3. The aqueous mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give the product (6) (10.0 g, 66.6%) which was pure by NMR analysis.

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