Hydrochloric Acid → Isopropyl 4-(3-bromophenylamino)-3-nitrobenzoate

HRID 581898

Reaktionsgleichung

Reaktionsgleichung von HRID 581898
Cl[C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[N+:14]([O-:16])=[O:15].[Br:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][CH:24]=1)[NH2:21].C(=O)([O-])[O-].[K+].[K+].Cl>CN1CCCC1=O>[Br:17][C:18]1[CH:19]=[C:20]([NH:21][C:2]2[CH:13]=[CH:12][C:5]([C:6]([O:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=2[N+:14]([O-:16])=[O:15])[CH:22]=[CH:23][CH:24]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 115623-BromoanilineHCID 693119Isopropyl 4-chloro-3-nitrobenzoate

Produkt 1

HCID 54019765Isopropyl 4-(3-bromophenylamino)-3-nitrobenzoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of i-propyl 4-chloro-3-nitrobenzoate (25.88 g, 0.11 mol), 3-bromoaniline (17.36 ml, 0.16 mol) and potassium carbonate (14.63 g, 0.11 mol) in N-methyl-2-pyrrolidone (25 ml) is heated to 150° C. for 3 days. After cooling the mixture is poured into diluted hydrochloric acid (300 ml, 1 M). The precipitate is filtered off, washed with water and dried (37.4 g). This crude product is washed with hot 2-propanol to afford pure 24 (26.25 g, 65%). Mp 162-165° C.

Aufarbeitung

  1. temperatureAfter cooling the mixture
  2. filtrationThe precipitate is filtered off
  3. washwashed with water
  4. customdried (37.4 g)
  5. washThis crude product is washed with hot 2-propanol

Quellen und Nachweise

ORD-Eintrag
ord-51be9a7f15b1460d834432182bba1ba0
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05922725

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