반응 #59107

반응 방정식

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

용매

DMF

THF

반응 조건

후처리

1. 1
   농축The reaction concentrated
2. 2
   workup.DISSOLUTIONthe resulting residue dissolved in EtOAc
3. 3
   세척The organic phase was washed with saturated aqueous NaHCO3 (3×)
4. 4
   추출the combined aqueous portions were extracted with EtOAc
5. 5
   농축The combined organic portions were concentrated
6. 6
   기타to give an orange residue as 2
7. 7
   기타the resulting reaction
8. 8
   온도maintained at rt for 14 h
9. 9
   기타the remaining solution was partitioned between EtOAc and water
10. 10
    기타The layers were separated
11. 11
    추출the aqueous phase extracted with EtOAc (3×)
12. 12
    농축The combined organic layers were concentrated
13. 13
    기타to give an orange solid as 3 which
14. 14
    기타was carried forward without further purification

실험 절차

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.

출처