2-Amino-6-methylpyridine → HCID 14368610, compound

HRID 2232113Notes

Reaction equation

HRID 2232113 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.C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:8][C:4]1[N:3]=[C:2]([NH:1][C:26]([C:11]2[C:10](=[O:9])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:12]=2)=[O:27])[CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 2

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

Product 1

HCID 14368610HCID 14368610, compound

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 6212ChloroformSolvent

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-quinolnecarboxamide 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
  5. customdichloromethane as the eluent) to afford 9.8 g of 1,2-dihydro-4-hydroxy-N-(6-methyl-2-pyridyl)-1-phenyl-3-quinolnecarboxamide which

Sources & evidence

ORD record
ord-b3696c7373154cff99158e2757ae39a9
Source dataset
uspto-grants-1988_11
Patent number
US04786644

Reaction notes

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