Reaktion #59107

Reaktionsgleichung

hydrazine monohydrate

Ethyl chloroformate

aniline

{[4-(4-Methylamino-3-nitro-phenoxy)-pyridin-2-ylcarbamoyl]-methyl}-carbamic acid tert-butyl ester

iPr2NEt

→

[4-(4-methylamino-3-nitro-phenoxy)-pyridin-2-yl]carbamic acid ethyl ester

Lösungsmittel

DMF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction concentrated
2. 2
   workup.DISSOLUTIONthe resulting residue dissolved in EtOAc
3. 3
   WaschenThe organic phase was washed with saturated aqueous NaHCO3 (3×)
4. 4
   Extraktionthe combined aqueous portions were extracted with EtOAc
5. 5
   EinengenThe combined organic portions were concentrated
6. 6
   Sonstigeto give an orange residue as 2
7. 7
   Sonstigethe resulting reaction
8. 8
   Temperaturmaintained at rt for 14 h
9. 9
   Sonstigethe remaining solution was partitioned between EtOAc and water
10. 10
    SonstigeThe layers were separated
11. 11
    Extraktionthe aqueous phase extracted with EtOAc (3×)
12. 12
    EinengenThe combined organic layers were concentrated
13. 13
    Sonstigeto give an orange solid as 3 which
14. 14
    Sonstigewas carried forward without further purification

Vorschrift

Ethyl chloroformate (2 eq.) was added to a stirring solution of aniline 1 (1 eq.) and iPr2NEt (2 eq.) in dry THF (14 mL) at 0° C. The reaction was allowed to warm to rt over 2 h. The reaction concentrated and the resulting residue dissolved in EtOAc. The organic phase was washed with saturated aqueous NaHCO3 (3×) and the combined aqueous portions were extracted with EtOAc. The combined organic portions were concentrated to give an orange residue as 2. The residue was dissolved in DMF (20 mL), hydrazine monohydrate (1 eq.) added and the resulting reaction maintained at rt for 14 h. The reaction volume was reduced and the remaining solution was partitioned between EtOAc and water. The layers were separated and the aqueous phase extracted with EtOAc (3×). The combined organic layers were concentrated to give an orange solid as 3 which was carried forward without further purification: LCMS m/z 333.3 (MH+), tR=2.29 min.

Quelle