2-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridine → HCID 178479199, compound

HRID 1654844Notes

Reaction equation

HRID 1654844 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([F:16])=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:17])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[C:19]1([CH2:25][C:26](=[NH:30])OCC)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)C>[ClH:17].[Cl:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([F:16])[C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:26](=[NH:30])[CH2:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 101062702-Amino-3-(2-chloro-6-fluorobenzyloxy)pyridineHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 178479199HCID 178479199, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2-chloro-6-fluorobenzyloxy)pyridine (5.05 g, 20 mmol) and ethyl phenylacetimidate hydrochloride (4.39 g, 22 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) and recrystallisation from ethanol/ether to obtain the product (1.53 g), m.p. 115°-123° 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) and recrystallisation from ethanol/ether

Sources & evidence

ORD record
ord-d3f6e1a28cb74e218d799101abb12f3e
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

Loading…