Diphenyl Ether → Ethyl 7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

HRID 503497Notes

Reaction equation

HRID 503497 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][CH:9]=[C:10]([C:16]([O:18]CC)=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[N:6][CH:7]=1.O(C1C=CC=CC=1)C1C=CC=CC=1>CC#N>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([C:16](=[O:18])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][NH:8]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 67318826Diethyl 2-((5-bromopyridin-3-ylamino)methylene)malonate

Product 1

HCID 13459134Ethyl 7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a RBF fitted with a reflux condenser a mixture of diethyl 2-((5-bromopyridin-3-ylamino)methylene)malonate (1 g, 3 mmol) and 1-phenoxybenzene (10 mL, 63 mmol) was heated to reflux for 1 h. The reaction mixture was allowed to cool to RT and CH3CN was added. The resulting solids were filtered and dried to provide the desired product as a light brown solid.

Workup

  1. customIn a RBF fitted with a reflux condenser
  2. temperaturewas heated
  3. temperatureto reflux for 1 h
  4. filtrationThe resulting solids were filtered
  5. customdried

Sources & evidence

ORD record
ord-8742c5ab8ec64fd49c32c07bffcc8527
Source dataset
uspto-grants-2010_08
Patent number
US07776857B2

Reaction notes

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