2-Amino-6-methylpyridine → HCID 54716316, compound

HRID 1089464Notes

Reaction equation

HRID 1089464 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:11]=1[C:26](OCC)=[O:27]>C1(C)C=CC=CC=1>[OH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:12][C:11]=1[C:26]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1)=[O:27]

Participants

4

Reactant 2

HCID 157652-Amino-6-methylpyridineHCID 85585358HCID 85585358, compound

Product 1

HCID 54716316HCID 54716316, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.49 g of 2-amino-6-methylpyridine and 10 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 500 ml of toluene was refluxed for 24 hours in a soxhlet apparatus containing 10 g of 4 Å molecular sieves. The solution was filtered and evaporated. The residue was purified by means of high pressure liquid chromatography (silica gel: dichloromethane as the eluent) to afford 9.8 g of 1,2-dihydro-4-hydroxy-N-(6-methyl-2-pyridyl)-1-phenyl-3-quinolinecarboxamide which was dissolved in chloroform, treated with 35 g of activated manganese dioxide and stirred for three hours at room temperature.

Workup

  1. additioncontaining 10 g of 4 Å molecular sieves
  2. filtrationThe solution was filtered
  3. customevaporated
  4. customThe residue was purified by means of high pressure liquid chromatography (silica gel

Sources & evidence

ORD record
ord-9ea41f4c434d471eb2c3b45794bd2c6d
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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