Hydrochloric Acid → HCID 12818610, compound

HRID 2285814Notes

Reaction equation

HRID 2285814 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[N:8]([CH3:17])[C:9]2[C:14]([C:15]=1Cl)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+].Cl>>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[O:18])[N:8]([CH3:17])[C:9]2[C:14]([C:15]=1[N:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1)=[CH:13][CH:12]=[CH:11][N:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 12818606HCID 12818606, compound

Product 1

HCID 12818610HCID 12818610, compound

Procedure

A stirred mixture of 5.2 g. (0.02 mole) of 4-chloro-1,2-dihydro-1-methyl-2-oxo-1,8-naphthyridine-3-carboxylic acid ethyl ester, 2.0 g. (0.02 mole) of N-methylpiperazine and 2.12 g. (0.02 mole) of sodium carbonate 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 50 ml. of a 20% aqueous sodium carbonate solution and was extracted with 50 ml. of ether. The ether layer was dried over magnesium sulfate, filtered, diluted with a few ml. of ethanol and was acidified with a saturated ethereal hydrochloric acid solution. The precipitate which formed was collected and was recrystallized from ethanol to afford 0.3 g. of product as the hydrochloride, hemihydrate, m.p. 231°-234° C. dec.

Workup

  1. additionA stirred mixture of 5.2 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 50 ml
  6. extractionof a 20% aqueous sodium carbonate solution and was extracted with 50 ml
  7. dry with materialThe ether layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. additiondiluted with a few ml
  10. customThe precipitate which formed
  11. customwas collected
  12. customwas recrystallized from ethanol
  13. customto afford 0.3 g

Sources & evidence

ORD record
ord-a8a0e8a6194f46d98b8cb4df6fc216bd
Source dataset
uspto-grants-1982_04
Patent number
US04324893

Reaction notes

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