Benzoic acid, 3-nitro-5-(4-pyridinyl)-, methyl ester → HCID 67497400, compound

HRID 1628282Notes

Reaction equation

HRID 1628282 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 46317472Benzoic acid, 3-nitro-5-(4-pyridinyl)-, methyl ester

Product 1

HCID 67497400HCID 67497400, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 3-nitro-5-(pyridin-4-yl)benzoate (45.1.B) (5.60 g, 21.62 mmol) in methanol (50 mL) was added 10% Pd on carbon by weight (2.50 g). The air was evacuated from the reaction flask and was replaced with hydrogen. The resulting slurry was stirred overnight at room temperature. The reaction mixture was then filtered and the mother liquor condensed to afford methyl 3-amino-5-(pyridin-4-yl)benzoate (45.1.C) (4.70 g, 95% yield) which was used in the next step without any further purification.

Workup

  1. customThe air was evacuated from the reaction flask
  2. filtrationThe reaction mixture was then filtered
  3. customthe mother liquor condensed

Sources & evidence

ORD record
ord-97098eac16c94e6abb8af39ea4354879
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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