Sodium Carbonate → HCID 12737476, compound

HRID 894819Notes

Reaction equation

HRID 894819 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][CH: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+]>C(O)C>[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][CH:10]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 531671-MethylpiperazineHCID 6061803-Quinolinecarboxylic acid, 1,2-dihydro-4-chloro-1-methyl-2-oxo-, ethyl ester

Product 1

HCID 12737476HCID 12737476, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 9.5 g. of 4-chloro-1,2-dihydro-1-methyl-2-oxo-3-quinolinecarboxylic acid ethyl ester, 3.6 g. of N-methylpiperazine and 3.8 g. of sodium carbonate in 50 ml. of ethanol was heated under reflux for 3 hours and filtered. The filtrate was taken to dryness on a rotary evaporator leaving a thick, tarry oily residue. On triturating the oil with diethyl ether, there was obtained 9.4 g. of impure title compound, m.p. 144°-148° C. Recrystallization from ethanol gave 5.5 g. of the title compound, m.p. 154°-156° C.

Workup

  1. additionA stirred mixture of 9.5 g
  2. temperatureunder reflux for 3 hours
  3. filtrationfiltered
  4. customThe filtrate was taken to dryness on a rotary evaporator
  5. customleaving a thick, tarry oily residue
  6. customOn triturating the oil with diethyl ether
  7. customthere was obtained 9.4 g

Sources & evidence

ORD record
ord-96c20730160c4097abc00dbd5c54421f
Source dataset
uspto-grants-1981_08
Patent number
US04284768

Reaction notes

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