反应详情

4-Chlorophenylhydrazine hydrochloride (2.105 g, 14.76 mmol) was suspended in EtOH (25 ml), treated with di-isopropylethylamine (2.253 ml, 12.93 mmol) and stirred for 30 minutes. Isatoic anhydride (1.918 g, 11.76 mmol) was added and the mixture was heated to reflux for 3 hours. The reaction mixture was cooled to room temperature and stirred overnight. The material was concentrated to dryness and the resulting residue was partitioned between EtOAc (˜25 ml) and 50% saturated NaCl (3×30 ml). The organic layer (also containing a small amount of emulsion which would not dissipate over 3 extractions) was dried over MgSO4 and concentrated to an orange solid. The material was triturated with EtOAc, filtered and rinsed with additional EtOAc. The filtrate was concentrated to dryness and treated with DCM (dichloromethane). The mixture was stirred overnight. The mixture was filtered, rinsed with DCM and the solid dried to provide 1.538 g (50%) of 2-amino-benzoic acid N′-(4-chloro-phenyl)-hydrazide (Intermediate 40) as a mauve-colored solid. MS (APCI): (M+1)=262.1, (M−1)=260.0.

1. temperaturethe mixture was heated
2. temperatureto reflux for 3 hours
3. stirringstirred overnight
4. concentrationThe material was concentrated to dryness
5. customthe resulting residue was partitioned between EtOAc (˜25 ml) and 50% saturated NaCl (3×30 ml)
6. additionThe organic layer (also containing a small amount of emulsion which would not
7. extractiondissipate over 3 extractions)
8. dry with materialwas dried over MgSO4
9. concentrationconcentrated to an orange solid
10. customThe material was triturated with EtOAc
11. filtrationfiltered
12. washrinsed with additional EtOAc
13. concentrationThe filtrate was concentrated to dryness
14. additiontreated with DCM (dichloromethane)
15. stirringThe mixture was stirred overnight
16. filtrationThe mixture was filtered
17. washrinsed with DCM
18. customthe solid dried