Ammonium Chloride → 3-(3-amino-4-chlorobenzylidene)-3H-isobenzofuran-1-one

HRID 459776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459776
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([CH:6]=[C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[O:8]2)=[CH:4][C:3]=1[N+:19]([O-])=O.[Cl-].[NH4+]>[Fe].O>[NH2:19][C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][C:2]=1[Cl:1])[CH:6]=[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 686228163-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one

Produkt 1

HCID 686232423-(3-amino-4-chlorobenzylidene)-3H-isobenzofuran-1-oneAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A stirred mixture of the above crude 3-(4-chloro-3-nitrobenzylidene)-3H-isobenzofuran-1-one (6.2 g), industrial methylated spirit (80 ml), water (60 ml) and ammonium chloride (2.14 g, 0.04 mol) was heated to 70° C., and iron powder (11.2 g, 0.2 gatom) was added in portions. When the addition was complete, the stirred mixture was heated under reflux for a further 2 hours, then it was filtered while hot through Celite. The collected inorganic solids were washed with hot industrial methylated spirit (3×150 ml), then the filtrate and washings were combined and the solvent was removed in vacuo. The residue was triturated with water (60 ml) and the resulting sticky solid was collected by filtration and triturated with industrial methylated spirit (80 ml). The resulting solid was collected by filtration, washed with industrial methylated spirit (2×1 ml) and dried in vacuo for 24 hours to give 3-(3-amino-4-chlorobenzylidene)-3H-isobenzofuran-1-one (3.58 g) as a yellow solid, m.pt. 148–153° C.; m/z (M+H)+. 272/274, 100% purity, which was used directly in the next stage.

Aufarbeitung

  1. additionWhen the addition
  2. temperaturethe stirred mixture was heated
  3. temperatureunder reflux for a further 2 hours
  4. filtrationit was filtered while hot through Celite
  5. washThe collected inorganic solids were washed with hot industrial methylated spirit (3×150 ml)
  6. customthe solvent was removed in vacuo
  7. customThe residue was triturated with water (60 ml)
  8. filtrationthe resulting sticky solid was collected by filtration
  9. customtriturated with industrial methylated spirit (80 ml)
  10. filtrationThe resulting solid was collected by filtration
  11. washwashed with industrial methylated spirit (2×1 ml)
  12. customdried in vacuo for 24 hours

Quellen und Nachweise

ORD-Eintrag
ord-ea164f5a061546fcafdf0e2f4d8a5760
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196085B2

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