Ethyl 4-methoxyphenylacetimidate hydrochloride → HCID 178490394, compound

HRID 1654820Notes

Reaction equation

HRID 1654820 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][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](=[NH:31])OCC)=[CH:22][CH:21]=1>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:27](=[NH:31])[CH2:26][C:23]2[CH:24]=[CH:25][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12238406Ethyl 4-methoxyphenylacetimidate hydrochlorideHCID 138258823-[(2-Methylphenyl)methoxy]pyridin-2-amine

Product 1

HCID 178490394HCID 178490394, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2-methylbenzyloxy)pyridine (5.2 g, 24.2 mmol) and ethyl 4-methoxyphenylacetimidate hydrochloride (6.1 g, 26.7 mmol) in ethanol (80 ml) was heated under reflux for 2 hours, then the solvent evaporated. The residue was taken up in chloroform, filtered to remove an insoluble solid, and the filtrate purified by flash chromatography (chloroform/methanol) to obtain the product (0.29 g), m.p. 58°-67° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe solvent evaporated
  4. filtrationfiltered
  5. customto remove an insoluble solid
  6. customthe filtrate purified by flash chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-8f92682bc1ff4204bcb6240808034b44
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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