Hydrochloric Acid → HCID 20570440, compound

HRID 1577938Notes

Reaction equation

HRID 1577938 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:20])[CH3:19])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[OH-].[Na+].[CH:24]1([C:30]([Cl:32])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.Cl>CC(C)=O>[ClH:32].[CH:24]1([C:30]([O:1][C:2]2[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:21])[CH2:16][NH:17][CH:18]([CH3:19])[CH3:20])=[C:6]3[C:11]=2[NH:10][C:9](=[O:12])[CH2:8][CH2:7]3)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 75938Cyclohexanecarbonyl chlorideHCID 12751813HCID 12751813, compound

Product 1

HCID 20570440HCID 20570440, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

0.66 g of 8-hydroxy-5-(2-hydroxy-3-isopropylaminopropoxy)-3,4-dihydrocarbostyril was suspended in 10 ml of acetone, and 3.0 ml of 1 N sodium hydroxide was added thereto to form a homogeneous solution. 0.35 g of cyclohexylcarbonyl chloride dissolved in a small amount of acetone was added dropwise to the solution while ice-cooling and stirring. After the reaction mixture was allowed to stand under ice-cooling for 30 minutes, 1 N hydrochloric acid was added thereto to adjust to a pH of 3. The solvent was evaporated under reduced pressure, and the residue was dissolved in water and extracted with chloroform. The aqueous layer was concentrated to dryness under reduced pressure, and the residue was purified by silica gel chromatography using chloroform-methanol (8:1 by volume) as an eluent. The solvent was evaporated, and the residue was recrystallized from methanol-diethyl ether to obtain 0.45 g of 8-cyclohexylcarbonyloxy-5-(2-hydroxy-3-isopropylaminopropoxy)-3,4-dihydrocarbostyril hydrochloride as colorless flake-like crystals having a melting point of 227°-228° C.

Workup

  1. customto form a homogeneous solution
  2. additionwas added dropwise to the solution while ice-
  3. temperaturecooling
  4. temperaturecooling for 30 minutes
  5. customThe solvent was evaporated under reduced pressure
  6. dissolutionthe residue was dissolved in water
  7. extractionextracted with chloroform
  8. concentrationThe aqueous layer was concentrated to dryness under reduced pressure
  9. customthe residue was purified by silica gel chromatography
  10. customThe solvent was evaporated
  11. customthe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-477756705f6647a5a7aa8e2caf28458a
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

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