Ethyl 2-phenylacetimidate hydrochloride → HCID 178479191, compound

HRID 1654838Notes

Reaction equation

HRID 1654838 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[C:15]([Cl:16])=[C:14]3[O:17][CH2:18][O:19][C:13]3=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[ClH:20].[C:21]1([CH2:27][C:28](=[NH:32])OCC)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(O)C>[ClH:16].[Cl:20][C:11]1[CH:12]=[C:13]2[O:19][CH2:18][O:17][C:14]2=[CH:15][C:10]=1[CH2:9][O:8][C:7]1[C:2]([NH:1][C:28](=[NH:32])[CH2:27][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 12218775Ethyl 2-phenylacetimidate hydrochlorideHCID 20077046HCID 20077046, compound

Product 1

HCID 178479191HCID 178479191, compoundYield 10.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Amino-3-(6-chloro-4,5-methylenedioxybenzyloxy)pyridine (6 g, 21.6 mmol) and ethyl phenylacetimidate hydrochloride (5.17 g, 26 mmol) in ethanol (150 ml) were heated under reflux for 3 hrs. The solvent was evaporated and the residue purified by flash chromatography (silica, 1% methanol/dichloromethane), trituration with ether and recrystallisation from ethanol to give the tire compound (1.0 g), m.p. 189° C. (softening 170° C.).

Workup

  1. temperatureunder reflux for 3 hrs
  2. customThe solvent was evaporated
  3. customthe residue purified by flash chromatography (silica, 1% methanol/dichloromethane), trituration with ether and recrystallisation from ethanol

Sources & evidence

ORD record
ord-b85e99f1721342d283e9f9e38255ea2f
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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