2-Aminopyridine → HCID 54716320, compound

HRID 1089452Notes

Reaction equation

HRID 1089452 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:11][C:10]=1[C:25](OCC)=[O:26]>C1(C)C=CC=CC=1>[OH:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:11][C:10]=1[C:25]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)=[O:26]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 85585358HCID 85585358, compound

Product 1

HCID 54716320HCID 54716320, compoundYield 75.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2.8 g of 2-aminopyridine and 4.2 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 190 ml of toluene was refluxed for 16 hours in a soxhlet apparatus containing 10 g of 4 Å molecular sieves. Evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel: 1:1 ethyl acetate-hexane as the eluent) to yield 3.7 g (73%) of 1,2-dihydro-4-hydroxy-1-phenyl-N-(2-pyridyl)-3-quinolinecarboxamide, m.p. 145° C. (dec).

Workup

  1. additioncontaining 10 g of 4 Å molecular sieves
  2. customEvaporation of the volatiles
  3. customafforded a residue which
  4. customwas purified by means of high pressure liquid chromatography (silica gel

Sources & evidence

ORD record
ord-e2971b598fcf4ee79a93dc6b8c121e7e
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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