Hydrochloric Acid → 2-[[2-(4-Carboxyphenyl)ethyl]amino]-5-chloro-3-nitrobenzoic acid

HRID 487200

Reaktionsgleichung

Reaktionsgleichung von HRID 487200
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([Cl:14])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(=O)([O-])[O-].[K+].[K+].[NH2:21][CH2:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=1.Cl>CO>[Cl:14][C:8]1[CH:9]=[C:10]([N+:11]([O-:13])=[O:12])[C:2]([NH:21][CH2:22][CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][CH:25]=2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 69512,5-Dichloro-3-nitrobenzoic acidHCID 11430Potassium CarbonateHCID 5060664-(2-Aminoethyl)benzoic acid

Produkt 1

HCID 542988122-[[2-(4-Carboxyphenyl)ethyl]amino]-5-chloro-3-nitrobenzoic acidAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2,5-dichloro-3-nitrobenzoic acid (23.6 g, 100 mmol), powdered potassium carbonate (41.1 g, 300 mmol), and 4-(aminoethyl)benzoic acid (60.04 g, 400 mmol) in 250 ml of methanol was refluxed under argon for 18 hours. The reaction mixture was poured into 650 ml of 10% aqueous hydrochloric acid solution. The solid was collected and triturated with ethyl acetate. The ethyl acetate extract was decanted, dried with magnesium sulfate and concentrated in vacuo to give 20.15 g (57.5%) of the title compound; mp 255°-257° C.

Aufarbeitung

  1. temperaturewas refluxed under argon for 18 hours
  2. customThe solid was collected
  3. customtriturated with ethyl acetate
  4. extractionThe ethyl acetate extract
  5. customwas decanted
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b6c7993ebd9f4a05b43ed91b3538a110
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05294631

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