Ethanol → HCID 12818617, compound

HRID 2285818Notes

Reaction equation

HRID 2285818 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:19])[N:8]([CH2:17][CH3:18])[C:9]2[C:14]([C:15]=1[NH2:16])=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])C.[OH-].[Na+].C(O)C>C(O)(=O)C>[NH2:16][C:15]1[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][CH3:18])[C:7](=[O:19])[C:6]=1[C:4]([OH:5])=[O:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 12818632HCID 12818632, compound

Product 1

HCID 12818617HCID 12818617, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 2 g. of 4-amino-1-ethyl-1,2-dihydro-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester in 20 ml. of 10% aqueous sodium hydroxide containing 5 ml. of ethanol was heated under reflux for 3 hours to saponify the ester. The solution was cooled and was acidified with glacial acetic acid. The precipitate which formed was collected, air dried, and was recrystallized from ethanol to give 0.4 g. of product, m.p. 245°-248° C.

Workup

  1. additionA stirred mixture of 2 g
  2. temperatureunder reflux for 3 hours
  3. temperatureThe solution was cooled
  4. customThe precipitate which formed
  5. customwas collected
  6. customair dried
  7. customwas recrystallized from ethanol
  8. customto give 0.4 g

Sources & evidence

ORD record
ord-112498deed8045c898b70b203c52bfed
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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