4-Anilino-3-nitrobenzoic acid → 3-Amino-4-phenylamino-benzoic acid

HRID 28664

Reaktionsgleichung

Reaktionsgleichung von HRID 28664
[NH:1]([C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=1[N+:17]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[Pd]>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[NH:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:12]([OH:14])=[O:13]

Komponenten

4

Edukt 1

HCID 38243664-Anilino-3-nitrobenzoic acid

Produkt 1

HCID 7738213-Amino-4-phenylamino-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of the 4-anilino-3-nitrobenzoic acid (20.1 mmol) in THF (100 mL) was charged with 10% Pd/C (500 mg) and the reaction flask evacuated and subsequently charged with H2 (g) three times. The mixture was stirred vigorously for 12 h after which time it was filtered through diatomaceous earth and the filtrate concentrated in vacuo to give the desired 3-amino-4-anilinobenzoic acid: e.g. 3-amino4-[(3-hydroxyphenyl)amino]benzoic acid.

Aufarbeitung

  1. customthe reaction flask evacuated
  2. additionsubsequently charged with H2 (g) three times
  3. filtrationwas filtered through diatomaceous earth
  4. concentrationthe filtrate concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0a653020fe1a4d3f9a6e01a5511e2f2e
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419995B2

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