Sodium Dithionite → 5-Amino-3-benzylamino-4-phenylbenzoic acid

HRID 1605544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1605544
[CH2:1]([NH:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([N+:24]([O-])=O)[C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(S([O-])=O)([O-])=O.[Na+].[Na+]>N1C=CC=CC=1.O>[NH2:24][C:16]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:9]([NH:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=[C:11]([CH:15]=1)[C:12]([OH:14])=[O:13]

Komponenten

5

Edukt 2

HCID 24489Sodium DithioniteHCID 124087723-Benzylamino-5-nitro-4-phenylbenzoic acid

Produkt 1

HCID 124087755-Amino-3-benzylamino-4-phenylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-benzylamino-5-nitro-4-phenylbenzoic acid (3.0 g) in a mixture of pyridine (15 ml) and water (15 ml), sodium dithionite (6.0 g) is added in portions during about 15 minutes. The mixture is heated on a steam bath for about 30 minutes, and is then evaporated in vacuo. The residue is treated with cold 1 N acetic acid (about 50 ml) and after cooling, the resulting precipitate is collected by filtration, washed with water and dried. After recrystallization twice from aqueous ethanol, 5-amino-3-benzylamino-4-phenylbenzoic acid is obtained with a melting point of 179°-181° C.

Aufarbeitung

  1. additionis added in portions during about 15 minutes
  2. temperatureThe mixture is heated on a steam bath for about 30 minutes
  3. customis then evaporated in vacuo
  4. additionThe residue is treated with cold 1 N acetic acid (about 50 ml)
  5. temperatureafter cooling
  6. filtrationthe resulting precipitate is collected by filtration
  7. washwashed with water
  8. customdried
  9. customAfter recrystallization twice from aqueous ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9ccb8f0ee595416895333397c0f562a4
Quelldatensatz
uspto-grants-1976_04
Patentnummer
US03950380

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