Reaktion #58680

Reaktionsgleichung

4-Chlorophenylhydrazine hydrochloride

di-isopropylethylamine

Isatoic anhydride

→

2-amino-benzoic acid N′-(4-chloro-phenyl)-hydrazide

Ausbeute 50.0%

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturto reflux for 3 hours
3. 3
   workup.STIRRINGstirred overnight
4. 4
   EinengenThe material was concentrated to dryness
5. 5
   Sonstigethe resulting residue was partitioned between EtOAc (˜25 ml) and 50% saturated NaCl (3×30 ml)
6. 6
   workup.ADDITIONThe organic layer (also containing a small amount of emulsion which would not
7. 7
   Extraktiondissipate over 3 extractions)
8. 8
   Trocknenwas dried over MgSO4
9. 9
   Einengenconcentrated to an orange solid
10. 10
    SonstigeThe material was triturated with EtOAc
11. 11
    Filtrationfiltered
12. 12
    Waschenrinsed with additional EtOAc
13. 13
    EinengenThe filtrate was concentrated to dryness
14. 14
    workup.ADDITIONtreated with DCM (dichloromethane)
15. 15
    workup.STIRRINGThe mixture was stirred overnight
16. 16
    FiltrationThe mixture was filtered
17. 17
    Waschenrinsed with DCM
18. 18
    Sonstigethe solid dried

Vorschrift

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.

Quelle