Tetrahydrofuran → 4,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl ester

HRID 216495

Reaktionsgleichung

Reaktionsgleichung von HRID 216495
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CCO.CO.[NH4+].[Cl-].C1COCC1>C(Cl)Cl.C1COCC1.O.[Zn]>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8]([NH2:10])[C:7]([NH2:13])=[C:6]([Cl:14])[C:5]=1[NH:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Komponenten

8

Edukt 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 18681192Ethanol, mixt. with methanolHCID 858681964-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester

Produkt 1

HCID 858681984,5-Diamino-3-chloro-2-phenylamino-benzoic acid methyl esterAusbeute 70,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittelHCID 21919333Tetrahydrofurane dichloromethaneLösungsmittel

Versuchsvorschrift

4-Amino-3-chloro-5-nitro-2-phenylamino-benzoic acid methyl ester 5c (0.50 g, 1.55 mmol) is dissolved into 2:1 EtOH/MeOH (15.5 mL). Saturated aqueous NH4Cl (15 mL), Zn powder (1.02 g, 15.6 mmol), and THF (10 mL) are added. After stirring for 20 hours, the reaction mixture is diluted with CH2Cl2/THF and water. The organic layer is washed with water (3×). The combined organic extracts are dried (Na2SO4) and concentrated under reduced pressure. The solids are triturated with ether to give 0.32 g (70%) clean desired product.

Aufarbeitung

  1. washThe organic layer is washed with water (3×)
  2. dry with materialThe combined organic extracts are dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe solids are triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-fe21fc11dc864a748873268ab9a1da4b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193229B2

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