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Ammonium Chloride → t-Butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate

HRID 895715
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895715
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([O:13][C:14]1[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:7]=[CH:6]2)#[N:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:27][C:24]1[CH:25]=[CH:26][C:14]([O:13][C:8]2[CH:7]=[CH:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:9]=2)=[C:15]([CH:23]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]
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Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 22380917t-Butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate

Produkt 1

HCID 22380961t-Butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

The compound (t-butyl 2-(6-cyano-2-naphthyloxy)-5-nitrobenzoate) (760 mg) obtained in a previous production example, iron powder (718 mg) and ammonium chloride (73 mg) were heated to reflux in ethanol:water (3:1, 30 ml) and reacted for 30 minutes. The insoluble portion was immediately filtered using celite, and the filtrate was concentrated. A saturated sodium bicarbonate solution was added to the obtained residue, and extraction was performed with ethyl acetate. The ethyl acetate layer was washed with saturated saline and then dried over magnesium sulfate, and the solvent was distilled off to obtain 736 mg of t-butyl 5-amino-2-(6-cyano-2-naphthyloxy)benzoate.

Aufarbeitung

  1. temperaturewere heated
  2. customreacted for 30 minutes
  3. filtrationThe insoluble portion was immediately filtered
  4. concentrationthe filtrate was concentrated
  5. additionA saturated sodium bicarbonate solution was added to the obtained residue, and extraction
  6. washThe ethyl acetate layer was washed with saturated saline
  7. dry with materialdried over magnesium sulfate
  8. distillationthe solvent was distilled off

Quellen und Nachweise

ORD-Eintrag
ord-cba85a63da3e417ba2d78b997d74018d
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06916837B2

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