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

HRID 1111619

Reaktionsgleichung

Reaktionsgleichung von HRID 1111619
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-8af6e775d9cb46f4831b64f9663c70d1
Quelldatensatz
uspto-grants-1978_10
Patentnummer
US04118397

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