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

HRID 1089457Notes

Reaction equation

HRID 1089457 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 43.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5.49 g of 2-amino-6-methylpyridine and 10.0 g of 1,2-dihydro-4-hydroxy-1-phenyl-3-quinolinecarboxylic acid, ethyl ester in 250 ml of toluene was refluxed overnight 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: 2% ethyl acetate-dichloromethane). The resultant solution was degassed and evaporated. Recrystallization of the residue from diethyl ether yielded 5.30 g (43%) of 1,2-dihydro-4-hydroxy-N-(6-methyl-2-pyridyl)-1-phenyl-3-quinolinecarboxamide, m.p. 74°-77° C.

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: 2% ethyl acetate-dichloromethane)
  5. customThe resultant solution was degassed
  6. customevaporated
  7. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-65d8fc0961584169b7a9158efe92e2aa
Source dataset
uspto-grants-1990_10
Patent number
US04966906

Reaction notes

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