Sodium Hydroxide → 2-{4-[2-(3,4-Dichloro-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid

HRID 488485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488485
C[O:2][C:3](=[O:30])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>CCO.C1COCC1>[Cl:29][C:24]1[CH:23]=[C:22]([CH2:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([NH:13][C:5]3[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=3[C:3]([OH:30])=[O:2])=[CH:15][CH:16]=2)[CH:27]=[CH:26][C:25]=1[Cl:28]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 537377402-{4-[2-(3,4-Dichloro-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid methyl ester

Produkt 1

HCID 99324612-{4-[2-(3,4-Dichloro-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-{4-[2-(3,4-dichloro-phenyl)-ethyl]phenylamino}-5-nitrobenzoic acid methyl ester (340 mg, 0.76 mmol) and 1N NaOH (aq.) (4.0 mL) in EtOH (4.0 mL) and THF (4.0 mL) was heated to reflux for 16 hours. The solvent was removed in vacuum. The residue was diluted with H2O and acidified with concentrated HCl to pH 1. The mixture was then extracted with methylene chloride, dried (Na2SO4), filtered and concentrated in vacuo to yield a yellow solid, 329 mg (0.76 mmol, 100%) of the desired product mp 214-217° C.

Aufarbeitung

  1. temperatureto reflux for 16 hours
  2. customThe solvent was removed in vacuum
  3. additionThe residue was diluted with H2O
  4. extractionThe mixture was then extracted with methylene chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f1c676206daa482c8d1737adb93f695d
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972287B1

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