2-Methoxyethylamine → HCID 54716188, compound

HRID 2058178Notes

Reaction equation

HRID 2058178 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][O:22][CH2:23][CH2:24][NH2:25]>C(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:25][CH2:24][CH2:23][O:22][CH3:21])=[O:5])[C:7]1=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 54737589HCID 54737589, compound

Product 1

HCID 54716188HCID 54716188, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 1.38 g. (0.005 mole) 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 0.75 g. (0.01 mole) of 2-methoxyethylamine in 20 ml. of ethanol was heated under reflux for 5 hours. The solution was left at room temperature overnight. The precipitate which formed was collected and was stirred in 100 ml. of a 20% aqueous acetic acid solution for 30 minutes. The insoluble material was collected, air dried and was recrystallized from heptane to give 0.9 g. of the title compound, m.p. 118°-20° C.

Workup

  1. additionA stirred mixture of 1.38 g
  2. temperatureunder reflux for 5 hours
  3. customThe precipitate which formed
  4. customwas collected
  5. waitof a 20% aqueous acetic acid solution for 30 minutes
  6. customThe insoluble material was collected
  7. customair dried
  8. customwas recrystallized from heptane
  9. customto give 0.9 g

Sources & evidence

ORD record
ord-a5449e6f770e4e5f9623c953542c929c
Source dataset
uspto-grants-1980_07
Patent number
US04215123

Reaction notes

Loading…