3-[(2-Methylphenyl)methoxy]pyridin-2-amine → HCID 178424274, compound

HRID 1654819Notes

Reaction equation

HRID 1654819 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:17].[CH3:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[CH2:25][C:26](=[NH:30])OCC>C(O)C>[ClH:17].[CH3:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:26](=[NH:30])[CH2:25][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:18])=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 138258823-[(2-Methylphenyl)methoxy]pyridin-2-amineHCID 20076957Ethyl 2-(2-methylphenyl)ethanimidate--hydrogen chloride (1/1)

Product 1

HCID 178424274HCID 178424274, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2-methylbenzyloxy)pyridine (5.2 g, 24.2 mmol) and ethyl 2-methylphenylacetimidate hydrochloride (5.7 g, 26.7 mmol) in ethanol (80 ml) was heated under reflux for 2 hours. Evaporation of the solvent gave an oil which was purified by flash chromatography (chloroform/methanol) to obtain the product (1.37 g), m.p. 147°-154° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customEvaporation of the solvent
  4. customgave an oil which
  5. customwas purified by flash chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-6be8a98d39094128ba932bdc6e62d7ee
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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