Dichlone → HCID 178516906, Verbindung

HRID 597603Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597603
ClC1C(=O)C2C(C(=[O:13])C=1Cl)=CC=CC=2.N([O-])=O.[Na+].[N+:19]([C:22]1[C:23](=[O:33])[C:24]2[C:29]([C:30](=[O:32])[CH:31]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2)([O-:21])=[O:20]>CO.O>[OH:13][C:31]1[C:30](=[O:32])[C:29]2[C:24]([C:23](=[O:33])[C:22]=1[N+:19]([O-:21])=[O:20])=[CH:25][CH:26]=[CH:27][CH:28]=2

Komponenten

6

Edukt 3

HCID 8342DichloneHCID 19016853Nitro naphthoquinoneHCID 23668193Sodium Nitrite

Produkt 1

HCID 178516906HCID 178516906, VerbindungAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A suspension of 2,3 -dichloro-1,4-naphthoquinone (6.83g; 0.03 mole) in methanol (40 ml) was stirred during the addition of a solution of sodium nitrite (6.9g; 0.1 mole) in water (50ml) and the mixture stirred at 80° C for 3 hours. Solution was attained after about 1 hr and the nitro naphthoquinone began to separate after 2 hrs. After cooling in ice and the yellow crystalline solid was filtered off, taken up in water (200ml), charcoalized and precipitated the product by addition of one-third the volume of concentrated hydrochloric acid, filtered off, washed well with 5N HCl and dried in vacuo over P2O5 /NaOH to give 5.30 g (81%) of material of m.p. 162°-163° C (d) which was identical to that prepared above.

Aufarbeitung

  1. waitSolution was attained after about 1 hr
  2. customto separate after 2 hrs
  3. temperatureAfter cooling in ice
  4. filtrationthe yellow crystalline solid was filtered off
  5. customprecipitated the product
  6. additionby addition of one-third the volume of concentrated hydrochloric acid
  7. filtrationfiltered off
  8. washwashed well with 5N HCl
  9. dry with materialdried in vacuo over P2O5 /NaOH

Quellen und Nachweise

ORD-Eintrag
ord-43cfdde7bf974cd88c1b60b3f51d9865
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014907

Notizen zur Reaktion

Wird geladen…