Methanol → HCID 54716190, compound

HRID 2058177Notes

Reaction equation

HRID 2058177 reaction equation
C(O[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:5])C.[CH3:21][NH2:22].CO.O>C(O)(=O)C>[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]([NH:22][CH3:21])=[O:5])[C:7]1=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 54737589HCID 54737589, compound

Product 1

HCID 54716190HCID 54716190, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 4 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) and 30 ml. of 40% aqueous methylamine in 20 ml. of methanol was heated under reflux for 5 hours. The solution was cooled, diluted with 100 ml. of water and was acidified with glacial acetic acid. The precipitate which formed was collected, air dried and was recrystallized from heptane to give 1.9 g. of the title compound, m.p. 150°-4° C.

Workup

  1. additionA stirred mixture of 4 g
  2. temperatureunder reflux for 5 hours
  3. temperatureThe solution was cooled
  4. additiondiluted with 100 ml
  5. customThe precipitate which formed
  6. customwas collected
  7. customair dried
  8. customwas recrystallized from heptane
  9. customto give 1.9 g

Sources & evidence

ORD record
ord-3998f6594ba845e783caab5cfcfb188e
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

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