HCID 10265056, compound → HCID 178479195, compound

HRID 1654856Notes

Reaction equation

HRID 1654856 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[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:16].[Cl:17][C:11]1[CH:12]=[C:13]([Cl:16])[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: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 10265056HCID 10265056, compoundHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 178479195HCID 178479195, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-(2,4-dichlorobenzyloxy)pyridine (5.07 g, 18.8 mmol) and ethyl phenylacetimidate hydrochloride (3.52 g, 25.8 mmol) in ethanol (150 ml) was heated under reflux for 2 hours. Evaporation of the solvent gave an oil which was purified by flash chromatography (dichloromethane/methanol) and trituration with ether to obtain the product (0.59 g), m.p. 185°-187° 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 (dichloromethane/methanol) and trituration with ether

Sources & evidence

ORD record
ord-172a3a01759446c4b7a925adbe2aa3ee
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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