2-Amino-4,6-dimethyl-5-phenylpyridine-3-carboxylic acid → 4,6-Dimethyl-5-phenyl-2-pyridylamine

HRID 1995615Notes

Reaction equation

HRID 1995615 reaction equation
[NH2:1][C:2]1[C:7](C(O)=O)=[C:6]([CH3:11])[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:18])[N:3]=1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[CH3:11][C:6]1[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:18])[N:3]=[C:2]([NH2:1])[CH:7]=1

Participants

4

Reactant 1

HCID 204025312-Amino-4,6-dimethyl-5-phenylpyridine-3-carboxylic acid

Product 1

HCID 135028544,6-Dimethyl-5-phenyl-2-pyridylamine

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

2-Amino-4,6-dimethyl-5-phenyl-3-pyridinecarboxylic acid (6.1 grams) and copper powder (1.0 gram) were heated in 50 ml quinoline at 270°-290° C. for approximately 3 hours. The entire reaction mixture was then chromatographed over 600 ml of Grace 923 silica gel with ether followed by ethyl acetate, yield 3.0 grams of dried product, m.p. 105°-112° C.

Workup

  1. customThe entire reaction mixture
  2. customwas then chromatographed over 600 ml of Grace 923 silica gel with ether

Sources & evidence

ORD record
ord-97c6b745c1c24bfb9d1ce0a5570878ae
Source dataset
uspto-grants-1983_09
Patent number
US04405552

Reaction notes

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