Sodium Hydroxide → HCID 18000177, compound

HRID 479852Notes

Reaction equation

HRID 479852 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-9c36b64fde334bf1b7a4dfd99f5871f9
Source dataset
uspto-grants-2003_11
Patent number
US06646124B2

Reaction notes

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