4-(2-Fluoro-5-methyl-pyridin-3-yl)-3,5-dinitro-benzoic acid methyl ester → 3,5-Diamino-4-(2-fluoro-5-methyl-pyridin-3-yl)-benzoic acid methyl ester

HRID 1642544Notes

Reaction equation

HRID 1642544 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[C:7]([C:13]2[C:14]([F:20])=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=2)=[C:6]([N+:21]([O-])=O)[CH:5]=1.[H][H]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:5]=[C:6]([NH2:21])[C:7]([C:13]2[C:14]([F:20])=[N:15][CH:16]=[C:17]([CH3:19])[CH:18]=2)=[C:8]([NH2:10])[CH:9]=1

Participants

5

Reactant 2

HCID 588801744-(2-Fluoro-5-methyl-pyridin-3-yl)-3,5-dinitro-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 588800593,5-Diamino-4-(2-fluoro-5-methyl-pyridin-3-yl)-benzoic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 128 (2.02, 6.03 mmol) was stirred in MeOH (150 mL) with 10% Pd/C (200 mg) under a balloon of hydrogen for 1.5 h. The reaction was filtered through Celite and concentrated to give 1.64 g (99%) of the title compound as a brown solid. MS (ES) [m+H] calc'd for C14H14FN3O2, 276; found 276.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-868639308def4473b1f9728e8b4bf454
Source dataset
uspto-grants-2012_02
Patent number
US08119655B2

Reaction notes

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