2-Amino-3-benzyloxypyridine → HCID 178510791, compound

HRID 1654811Notes

Reaction equation

HRID 1654811 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.Cl.[C:17]1([CH2:23][C:24](=[NH:28])OCC)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:9]([O:8][C:7]1[C:2]([NH:1][C:24](=[NH:28])[CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 903342-Amino-3-benzyloxypyridineHCID 12218775Ethyl 2-phenylacetimidate hydrochloride

Product 1

HCID 178510791HCID 178510791, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-3-benzyloxypyridine (2.5 g, 12.5 mmol) and ethyl phenylacetimidate hydrochloride (2.5 g, 12.5 mmol) in ethanol (100 ml) was heated under reflux for 1 hour. The solvent was evaporated in vacuo, and the residue taken up in chloroform, washed with aqueous sodium bicarbonate, dried and the chloroform evaporated. Treatment with charcoal and recrystallisation from ethyl acetate/petroleum ether gave the product (0.62 g), m.p. 114°-116° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was evaporated in vacuo
  4. washwashed with aqueous sodium bicarbonate
  5. customdried
  6. customthe chloroform evaporated
  7. customTreatment with charcoal and recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-9c36860c719f4ba2812b64b5221cd768
Source dataset
uspto-grants-1995_04
Patent number
US05409943

Reaction notes

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