Methyl 2-(3-(bis(4-methoxyphenyl)methylamino)-2-nitrophenoxy)-4-fluorobenzoate → Methyl 2-(2-amino-3-(bis(4-methoxyphenyl)methylamino)phenoxy)-4-fluorobenzoate

HRID 624435Notes

Reaction equation

HRID 624435 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH:18][C:19]2[C:20]([N+:37]([O-])=O)=[C:21]([CH:34]=[CH:35][CH:36]=2)[O:22][C:23]2[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:24]=2[C:25]([O:27][CH3:28])=[O:26])[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1>CO.[Ni]>[NH2:37][C:20]1[C:19]([NH:18][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:36][CH:35]=[CH:34][C:21]=1[O:22][C:23]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:24]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 1

HCID 67146178Methyl 2-(3-(bis(4-methoxyphenyl)methylamino)-2-nitrophenoxy)-4-fluorobenzoate

Product 1

HCID 67145036Methyl 2-(2-amino-3-(bis(4-methoxyphenyl)methylamino)phenoxy)-4-fluorobenzoate

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of EXAMPLE 368B (1.1 g) in methanol was hydrogenated over Raney Ni, at 60 psi of H2 at room temperature. The filtered solution was concentrated to give the title compound.

Workup

  1. concentrationThe filtered solution was concentrated

Sources & evidence

ORD record
ord-1343ab081ff944eebc307093e1d97109
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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