Cyclohexanecarbonyl chloride → HCID 21326339, compound

HRID 26032Notes

Reaction equation

HRID 26032 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[CH:14]1([C:20](Cl)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>N1C=CC=CC=1>[CH:14]1([C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([OH:13])=[C:6]3[C:11]=2[NH:10][C:9](=[O:12])[CH2:8][CH2:7]3)=[O:21])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 75938Cyclohexanecarbonyl chlorideHCID 213263108-Amino-5-hydroxy-3,4-dihydrocarbostyril

Product 1

HCID 21326339HCID 21326339, compoundYield 38.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

10.7 g of 8-amino-5-hydroxy-3,4-dihydrocarbostyril was dissolved in 100 ml of pyridine, and 10.0 g of cyclohexylcarbonyl chloride was added to the solution while vigorously stirring at room temperature followed by stirring at 50° C. for 30 minutes. The precipitated crystals were recovered by filtration, washed with ethanol, dried and dissolved in 200 ml of a 10% aqueous sodium hydroxide solution. Activated carbon was added to the solution, and the mixture was stirred and filtered. The filtrate was rendered acidic with hydrochloric acid under ice cooling, and the precipitated crystals were recovered by filtration, washed with water and dried. Recrystallization from methanol yielded 6.6 g of 8-cyclohexylcarbonylamino-5-hydroxy-3,4-dihydrocarbostyril as colorless amorphous crystals having a melting point of 304.2°-304.8° C.

Workup

  1. stirringby stirring at 50° C. for 30 minutes
  2. filtrationThe precipitated crystals were recovered by filtration
  3. washwashed with ethanol
  4. customdried
  5. dissolutiondissolved in 200 ml of a 10% aqueous sodium hydroxide solution
  6. additionActivated carbon was added to the solution
  7. stirringthe mixture was stirred
  8. filtrationfiltered
  9. filtrationthe precipitated crystals were recovered by filtration
  10. washwashed with water
  11. customdried
  12. customRecrystallization from methanol

Sources & evidence

ORD record
ord-ed3e672efcb94cddae4823c564ec1843
Source dataset
uspto-grants-1979_04
Patent number
US04147869

Reaction notes

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