Isatoic Anhydride → 2-amino-N'-(4-chlorophenyl)benzohydrazide

HRID 1723838Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723838
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[C:20]12[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[NH:25]C(=O)O[C:21]2=[O:22]>CCO>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH:10][C:21](=[O:22])[C:20]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[NH2:25])=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 8359Isatoic AnhydrideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 81531Diisopropylethylamine

Produkt 1

HCID 218205992-amino-N'-(4-chlorophenyl)benzohydrazideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-da29d91285fd4e2b82e5e23b0cd2601a
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485636B2

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