Sodium Chloride → HCID 13112626, compound

HRID 1154951Notes

Reaction equation

HRID 1154951 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.CC[O-].[Na+].[I-].[Na+].[CH3:19][N:20]([C:27](=[O:32])[CH2:28][CH2:29][CH2:30]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na+].[Cl-]>C(O)C>[CH3:19][N:20]([C:27]([CH2:28][CH2:29][CH2:30][O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2)=[O:32])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 1770652,6-DihydroxyquinolineHCID 2723922Sodium ethoxideHCID 16780864HCID 16780864, compound

Product 1

HCID 13112626HCID 13112626, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.6 Grams of 6-hydroxycarbostyril, 0.7 g of sodium ethylate, 1.6 g of sodium iodide and 2.4 g of N-methyl-N-(4-chlorobutyryl)aniline are added to 30 ml of ethanol and refluxed under agitation for 6 hours. After the reaction, the reaction solution is poured into 200 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The obtained crude crystals are recrystallized from chloroform-petroleum ether to obtain 1.3 g of 6-[3-(N-methylanilinocarbonyl)propoxy]carbostyril in the form of colorless needle-like crystals with melting point of 187°-189° C.

Workup

  1. temperaturerefluxed under agitation for 6 hours
  2. customAfter the reaction
  3. filtrationthe precipitated crystals are filtered out
  4. washwashed with water
  5. customThe obtained crude crystals
  6. customare recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-7efa203162a64360b87bef4a04b4e675
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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