Methyl 2-nitrobenzoate → 3-(1-Pyrrolidinyl)-4-phenoxy-5-amino-benzoic acid methyl ester

HRID 839055

Reaktionsgleichung

Reaktionsgleichung von HRID 839055
COC(=O)C1C=CC=CC=1[N+]([O-])=O.[CH3:14][O:15][C:16](=[O:38])[C:17]1[CH:22]=[C:21]([N+:23]([O-])=O)[C:20]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:18]=1>O1CCOCC1.[Ni]>[CH3:14][O:15][C:16](=[O:38])[C:17]1[CH:22]=[C:21]([NH2:23])[C:20]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]([N:33]2[CH2:34][CH2:35][CH2:36][CH2:37]2)[CH:18]=1

Komponenten

5

Edukt 2

HCID 69072Methyl 2-nitrobenzoateHCID 124983403-(1-Pyrrolidinyl)-4-phenoxy-5-nitrobenzoic acid methyl ester

Produkt 1

HCID 124983413-(1-Pyrrolidinyl)-4-phenoxy-5-amino-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of 30 g of the nitrobenzoic acid methyl ester obtained according to (b) in 500 ml of dioxane is hydrogenated catalytically in the presence of Raney nickel. After completion of the absorption of hydrogen, the whole is filtered and the filtrate is concentrated. The residue yields, on recrystallization from methanol, the desired compound in the form of colourless crystals melting at 153°-156° C in a very good yield.

Aufarbeitung

  1. customAfter completion of the absorption of hydrogen
  2. filtrationthe whole is filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue yields, on recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-03670224eb4545edb7313e82c3c53f75
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04093735

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