Sodium Chloride → HCID 13200333, compound

HRID 1154952Notes

Reaction equation

HRID 1154952 reaction equation
[Na].[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]2.[I-].[Na+].Cl[CH2:17][CH2:18][CH2:19][C:20]([NH:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:21].[Na+].[Cl-]>CO>[CH:23]1([NH:22][C:20]([CH2:19][CH2:18][CH2:17][O:2][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[NH:9][C:8](=[O:13])[CH2:7][CH2:6]3)=[O:21])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 27740406-Hydroxy-3,4-dihydro-2(1H)-quinolinoneHCID 41034704-chloro-N-cyclohexylbutanamideHCID 5360545Sodium

Product 1

HCID 13200333HCID 13200333, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 Gram of metallic sodium is dissolved in 50 ml of methanol under ice cooling, and to this solution is added 3.2 g of 6-hydroxy-3,4-dihydrocarbostyril, 3.2 g of sodium iodide and 4.6 g of N-(4-chlorobutyryl)cyclohexylamine, followed by 5-hour refluxing under agitation. After the reaction, the reaction solution is poured into 400 ml of saturated NaCl solution and the precipitated crystals are filtered out and washed with water. The resultant crude crystals are recrystallized from methanol to obtain 3.1 g of 6-[3-(N-cyclohexylaminocarbonyl)propoxy]-3,4-dihydrocarbostyril in the form of colorless needle-like crystals with melting point of 220°-221° C.

Workup

  1. waitfollowed by 5-hour
  2. temperaturerefluxing under agitation
  3. customAfter the reaction
  4. filtrationthe precipitated crystals are filtered out
  5. washwashed with water
  6. customThe resultant crude crystals are recrystallized from methanol

Sources & evidence

ORD record
ord-767d84464c8f4f1487761ec1adf8161c
Source dataset
uspto-grants-1981_11
Patent number
US04298739

Reaction notes

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