Ammonia → HCID 54717196, compound

HRID 2058176Notes

Reaction equation

HRID 2058176 reaction equation
C([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([CH2:18][CH3:19])[C:9]2[C:14]([C:15]=1[OH:16])=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=O)C.[NH3:21]>>[CH2:18]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)[C:15]([OH:16])=[C:6]([C:4]([NH2:21])=[O:3])[C:7]1=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 222AmmoniaHCID 54737589HCID 54737589, compound

Product 1

HCID 54717196HCID 54717196, compound

Procedure

A mixture of 1 g. of 1-ethyl-1,2-dihydro-4-hydroxy-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester (prepared as in Example 1) in 20 ml. of a saturated ethanolic ammonia solution was heated in an autoclave placed in a steam bath for 4 hours. The mixture was cooled and was filtered. The filter cake was triturated with 50 ml. of a 20% aqueous acetic acid solution. The insoluble material was collected, air dried and was recrystallized from ethanol to afford 0.4 g. of the title compound, m.p. 240°-2° C.

Workup

  1. additionA mixture of 1 g
  2. temperatureThe mixture was cooled
  3. filtrationwas filtered
  4. customThe filter cake was triturated with 50 ml
  5. customThe insoluble material was collected
  6. customair dried
  7. customwas recrystallized from ethanol
  8. customto afford 0.4 g

Sources & evidence

ORD record
ord-90b5728284284fed9d4d2136c53e191f
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

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