Sodium Hydroxide → HCID 18000177, compound

HRID 1856713Notes

Reaction equation

HRID 1856713 reaction equation
[CH2:1]([NH:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]([C:19]([O:21]CC)=[O:20])[C:12]2=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl-].[NH4+]>C(O)C>[CH2:1]([NH:8][C:9]1[N:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[C:13]([C:19]([OH:21])=[O:20])[C:12]2=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 18000183HCID 18000183, compound

Product 1

HCID 18000177HCID 18000177, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 6-benzylamino-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylate (60 mg), 1N NaOH (2 mL), and ethanol (0.5 mL) was heated at reflux for 2 h. The reaction mixture was cooled in an ice bath and saturated aqueous ammonium chloride was added. The resulting precipitate was collected, rinsed with water and ether, then dried to afford 35 mg of 6-benzylamino-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carboxylic acid as a brown solid.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. customThe resulting precipitate was collected
  5. washrinsed with water and ether
  6. customdried

Sources & evidence

ORD record
ord-1792d81773cf49bb8a6093e0fc1acb23
Source dataset
uspto-grants-2000_11
Patent number
US06143760

Reaction notes

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