Pyridine → 5-(1-Hydroxy-2-isopropylaminobutyl)-8-isobutyryloxycarbostyril hydrochloride

HRID 27777

Reaction equation

HRID 27777 reaction equation
N1C=CC=CC=1.[OH:7][CH:8]([C:16]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH3:11].[C:28]([Cl:33])(=[O:32])[CH:29]([CH3:31])[CH3:30]>C(OCC)C>[ClH:33].[OH:7][CH:8]([C:16]1[CH:25]=[CH:24][C:23]([O:26][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20](=[O:27])[NH:21]2)[CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])[CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 49168-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinoneHCID 62325Isobutyryl chloride

Product 1

HCID 233420555-(1-Hydroxy-2-isopropylaminobutyl)-8-isobutyryloxycarbostyril hydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

12 ml of pyridine was added to 0.4 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril, and 0.6 ml of isobutyryl chloride was added dropwise to the mixture while cooling with ice-water and stirring followed by stirring for 3 hours. After addition of about 200 ml of diethyl ether, the precipitate formed was washed thoroughly with diethyl ether and dissolved in 50 ml of water. The solution was washed with dichloroethane and the aqueous layer was concentrated to dryness. Acetone was added to the residue to crystallize the product which was then recrystallized from acetone to obtain 0.33 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-isobutyryloxycarbostyril hydrochloride having a melting point of 228°-229° C. (with coloration and decomposition).

Workup

  1. additionwas added dropwise to the mixture
  2. stirringby stirring for 3 hours
  3. customthe precipitate formed
  4. washwas washed thoroughly with diethyl ether
  5. dissolutiondissolved in 50 ml of water
  6. washThe solution was washed with dichloroethane
  7. concentrationthe aqueous layer was concentrated to dryness
  8. additionAcetone was added to the residue
  9. customto crystallize the product which
  10. customwas then recrystallized from acetone

Sources & evidence

ORD record
ord-1b787f008ecd4db989e2ecf98320ecd7
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Linked notes

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