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

HRID 971885

Reaction equation

HRID 971885 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

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 recrystallisation from methanol, the desired compound in the form of colourless crystals melting at 153°-156° C. in a very good yield.

Workup

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

Sources & evidence

ORD record
ord-b424b0d719a841f7ab5021decdefa98c
Source dataset
uspto-grants-1979_07
Patent number
US04161531

Linked notes

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