Methane → HCID 178524700, compound

HRID 1042762Notes

Reaction equation

HRID 1042762 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14]CC)=[O:13])=[CH:8][NH:9]2)=[N:4][CH:3]=1.[OH-].[Na+].C>O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([OH:17])=[C:7]([C:12]([OH:14])=[O:13])[CH:8]=[N:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 13459134Ethyl 7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 178524700HCID 178524700, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 7-bromo-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (1 g, 3 mmol) and 2.5 M NaOH (10 mL) were refluxed for 1 h in a RBF fitted with a reflux condenser. The hot, heterogeneous mixture was diluted with boiling water at which point a tan precipitate dissolved. Charcoal was added to the solution, which was swirled for 2 min and then the mixture was filtered. Glacial acetic acid was added to the filtrate and a white precipitate started to form (pH adjusted to 4). The precipitate was filtered off upon cooling, washed with water and dried to provide the desired product as a white solid.

Workup

  1. customfitted with a reflux condenser
  2. dissolutiondissolved
  3. filtrationthe mixture was filtered
  4. additionGlacial acetic acid was added to the filtrate
  5. customto form (pH adjusted to 4)
  6. filtrationThe precipitate was filtered off
  7. temperatureupon cooling
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-856a2398122641d887534ade4ff4ca3b
Source dataset
uspto-grants-2013_10
Patent number
US08557816B2

Reaction notes

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