N-methoxy-N-methyl-4-nitro-2'-methoxymethoxy-6'-methoxy-biphenyl-2-carboxamide → n-Methoxy-n-methyl-4-amino-2'-methoxymethoxy-6'methoxy-biphenyl-2-carboxamide

HRID 1358114Notes

Reaction equation

HRID 1358114 reaction equation
[CH3:1][O:2][N:3]([CH3:27])[C:4]([C:6]1[C:7]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH2:24][O:25][CH3:26])=[CH:8][CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)=[O:5]>CO.[Pd]>[CH3:1][O:2][N:3]([CH3:27])[C:4]([C:6]1[C:7]([C:15]2[C:20]([O:21][CH3:22])=[CH:19][CH:18]=[CH:17][C:16]=2[O:23][CH2:24][O:25][CH3:26])=[CH:8][CH:9]=[C:10]([NH2:12])[CH:11]=1)=[O:5]

Participants

4

Reactant 1

HCID 18189308N-methoxy-N-methyl-4-nitro-2'-methoxymethoxy-6'-methoxy-biphenyl-2-carboxamide

Product 1

HCID 18189391n-Methoxy-n-methyl-4-amino-2'-methoxymethoxy-6'methoxy-biphenyl-2-carboxamideYield 104.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of Example 5B (5.67 g.) was dissolved in methanol (120 mL) and hydrogenated at 4 atm with 10% Pd/C (0.60 g) for 1 hour. The catalyst was removed by filtration and the solution concentrated to give the titled compound (5.44 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe solution concentrated

Sources & evidence

ORD record
ord-7a807d22a9be40d1bc313867527b100d
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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