Pyridine → 5-Acetylaminonaphthalene-2-sulfonic acid

HRID 480671

Reaktionsgleichung

Reaktionsgleichung von HRID 480671
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:7]2.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23].[Na]>CO.C(OCC)C>[C:22]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:7]2)(=[O:24])[CH3:23]

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 84081,6-Cleve's acid2×HCID 5360545Sodium

Produkt 1

HCID 2355515-Acetylaminonaphthalene-2-sulfonic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 29.3 g (0.13 mol) of 5-amino-2-naphthalenesulfonic Acid (Compound 72) was added 40 mL of pyridine and 26 mL of acetic anhydride. The resulting suspension was allowed to stir at ambient temperature. After 24 hr, the resulting solution was diluted with 60 mL of methanol. Then, a solution of 3.6 g (0.156 mol) of sodium in 100 mL of methanol was added. After a solid precipitate began to form, 200 mL of diethyl ether was added and the suspension allowed to stir. The solid was collected by vacuum filtration and was washed with diethyl ether. This provided 38.9 g (0.11 mol) of the desired product. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

Aufarbeitung

  1. customto form
  2. stirringto stir
  3. filtrationThe solid was collected by vacuum filtration
  4. washwas washed with diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-d48ea52bf46f4dc390b20558ae0dbe8b
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653321B1

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