N,N-Dimethylaniline → 6-Chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid

HRID 1584045

Reaktionsgleichung

Reaktionsgleichung von HRID 1584045
[CH2:1]([O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1)[CH2:2][CH3:3].Cl[C:13]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[C:18]([Cl:25])[C:14]=1[C:15]([OH:17])=[O:16].CN(C)C1C=CC=CC=1>C(Cl)(Cl)Cl>[Cl:25][C:18]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([NH:9][C:8]2[CH:10]=[CH:11][C:5]([O:4][CH2:1][CH2:2][CH3:3])=[CH:6][CH:7]=2)[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=1

Komponenten

5

Edukt 3

HCID 949N,N-DimethylanilineHCID 78221Benzenamine, 4-propoxy-HCID 3506232,6-Dichloro-3-nitrobenzoic acid

Produkt 1

HCID 135883416-Chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 24.5 g of 4-propoxyaniline, 19.8 g of 2,6-dichloro-3-nitrobenzoic acid, and 150 ml N,N-dimethylaniline was heated under nitrogen at 100° overnight. The cooled reaction mixture was treated with dilute base and chloroform. After the aqueous layer was washed several times with chloroform, it was treated with hydrochloric acid and the resulting orange needles were collected by filtration and washed with water to give 6-chloro-3-nitro-2-[(4-propoxyphenyl)amino]benzoic acid, mp 194°-196° C.

Aufarbeitung

  1. temperaturewas heated under nitrogen at 100° overnight
  2. customThe cooled reaction mixture
  3. additionwas treated
  4. washAfter the aqueous layer was washed several times with chloroform, it
  5. additionwas treated with hydrochloric acid
  6. filtrationthe resulting orange needles were collected by filtration
  7. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-17e023e6bf2d48cc8637061859d580f8
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04555572

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