Hydrochloric Acid → HCID 20570440, compound

HRID 1577930Notes

Reaction equation

HRID 1577930 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. To the resulting solution was added dropwise 0.35 g of cyclohexylcarbonyl chloride dissolved in a small amount of acetone under ice-cooling and stirring. After the reaction mixture was allowed to stand under ice-cooling for 30 minutes, the mixture was adjusted to a pH of 3 with 1 N hydrochloric acid. The solvent was evaporated, and the residue was dissolved in water and then extracted with chloroform. The aqueous layer was concentrated to dryness under reduced pressure, and the residue was subjected to 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. temperaturecooling
  3. temperaturecooling for 30 minutes
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in water
  6. extractionextracted with chloroform
  7. concentrationThe aqueous layer was concentrated to dryness under reduced pressure
  8. customThe solvent was evaporated
  9. customthe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-5a6b0cf336164667bd7b79758ec1f9e3
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

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