3-[(4-Methoxybenzyl)oxy]pyridin-2-amine → HCID 178491290, compound

HRID 1654828Notes

Reaction equation

HRID 1654828 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[CH3:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][C:27](=[NH:31])OCC>C(O)C.C(Cl)(Cl)Cl>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:7]2[C:2]([NH:1][C:27](=[NH:31])[CH2:26][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH3:19])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 2

HCID 27283893-[(4-Methoxybenzyl)oxy]pyridin-2-amineHCID 20076957Ethyl 2-(2-methylphenyl)ethanimidate--hydrogen chloride (1/1)

Product 1

HCID 178491290HCID 178491290, compoundYield 5.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 2-amino-3-(4-methoxybenzyloxy)pyridine (4.6 g, 20 mmol) and ethyl 2methylphenylacetimidate hydrochloride (4.69 g, 22 mmol) in ethanol (80 ml) was heated under reflux for 2 hours. Evaporation of the solvent gave an oil which was taken up in chloroform, convened to the free base by washing with aqueous sodium bicarbonate, and purified by flash chromatography (chloroform/methanol) to obtain the product as a gum (0.38 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customEvaporation of the solvent
  4. customgave an oil which
  5. washby washing with aqueous sodium bicarbonate
  6. custompurified by flash chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-cccce6ab548b4b878ad48a8228bb8d38
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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