Hydrochloric Acid → HCID 12818647, compound

HRID 2285831Notes

Reaction equation

HRID 2285831 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:20])[N:8]([CH2:18][CH3:19])[C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=[O:5])[CH3:2].[CH3:21][N:22]([CH3:27])[CH2:23][CH2:24][CH2:25][NH2:26].C(=O)([O-])[O-].[Na+].[Na+].Cl>C(O)C>[CH2:1]([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[NH:26][CH2:25][CH2:24][CH2:23][N:22]([CH3:27])[CH3:21])=[CH:13][CH:12]=[C:11]([CH3:17])[N:10]=2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7993N,N-Dimethyl-1,3-propanediamineHCID 10340Sodium CarbonateHCID 12818638HCID 12818638, compound

Product 1

HCID 12818647HCID 12818647, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 8.7 g. (0.03 mole) of 1-ethyl-1,2-dihydro-4-chloro-7-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, (Example 30) 3.06 g. (0.03 mole) of 3-dimethylaminopropylamine and 3.18 g. of sodium carbonate in 100 ml. of ethanol was heated under reflux for 5 hours. The mixture was filtered and the filtrate was evaporated in a rotary evaporator. The residue was triturated with 150 ml. of water and was extracted with 150 ml. of diethyl ether. The ether layer was dried over magnesium sulfate, filtered and the ether was evaporated. The residue was passed through a neutral aluminum oxide column using ethyl acetate as the eluent. The ethyl acetate was evaporated and the residue was dissolved in anhydrous diethyl ether and the solution was acidified with an ethereal hydrochloric acid solution. The precipitate which formed was collected and was dried to give 1.9 g. of product as the hydrochloride, monohydrate, m.p. 75° C.

Workup

  1. additionA stirred mixture of 8.7 g
  2. temperatureunder reflux for 5 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated in a rotary evaporator
  5. customThe residue was triturated with 150 ml
  6. extractionof water and was extracted with 150 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe ether was evaporated
  10. customThe ethyl acetate was evaporated
  11. dissolutionthe residue was dissolved in anhydrous diethyl ether
  12. customThe precipitate which formed
  13. customwas collected
  14. customwas dried
  15. customto give 1.9 g

Sources & evidence

ORD record
ord-21b3d4565c0149e1ab220375aa39b087
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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