Hydrochloric Acid → HCID 12751826, compound

HRID 1577929Notes

Reaction equation

HRID 1577929 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:22])[CH2:16][NH:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[OH-].[Na+].[C:25]([Cl:28])(=[O:27])[CH3:26].Cl>CC(C)=O>[ClH:28].[C:25]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][CH2:14][CH:15]([OH:22])[CH2:16][NH:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 1246888-Hydroxycarteolol

Product 1

HCID 12751826HCID 12751826, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

0.7 g of 8-hydroxy-5-(3-t-butylamino-2-hydroxypropoxy)-3,4-dihydrocarbostyril was suspended in 20 ml of acetone, and 3.0 ml of 1 N NaOH was added to the suspension to form a homogeneous solution. 0.2 g of acetyl chloride dissolved in a small amount of acetone was added dropwise to the solution under ice-cooling and stirring. After the mixture was allowed to stand under ice-cooling for 30 minutes, 2 ml of 1 N hydrochloric acid was added to the mixture, and the solvent evaporated under reduced pressure. The residue was purified by silica gel column 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 0.4 g of 8-acetoxy-5-(3-t-butylamino-2-hydroxypropoxy)-3,4-dihydrocarbostyril hydrochloride as colorless flake-like crystals having a melting point of 247°-248° C. (with decomposition).

Workup

  1. customto form a homogeneous solution
  2. additionwas added dropwise to the solution under ice-
  3. temperaturecooling
  4. temperaturecooling for 30 minutes
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated
  8. customthe residue was recrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-526c46220ce34b2e9b167baf0a111509
Source dataset
uspto-grants-1981_09
Patent number
US04289883

Reaction notes

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