8-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinone → 5-(1-Hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxycarbostyril

HRID 27780

Reaction equation

HRID 27780 reaction equation
[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:21])[NH:15]2)[CH:3]([NH:6][CH:7]([CH3:9])[CH3:8])[CH2:4][CH3:5].[CH3:22][O-:23].[Na+]>CO>[OH:1][CH:2]([C:10]1[CH:19]=[CH:18][C:17]([O:20][C:22](=[O:23])[C:17]2[CH:18]=[CH:19][C:10]([CH3:2])=[CH:11][CH:16]=2)=[C:16]2[C:11]=1[CH:12]=[CH:13][C:14](=[O:21])[NH:15]2)[CH:3]([NH:6][CH:7]([CH3:9])[CH3:8])[CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 49168-Hydroxy-5-(1-hydroxy-2-((1-methylethyl)amino)butyl)-2(1H)-quinolinoneHCID 10942334Sodium Methoxide

Product 1

HCID 233420685-(1-Hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxycarbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.8 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-hydroxycarbostyril was dissolved in 150 ml of methanol, and a 15% methanolic solution of sodium methylate was added to the solution in an equimolar amount relative to the starting carbostyryl compound. The mixture was concentrated to dryness and the resulting residue was dissolved in 100 ml of dimethylformamide. 3.0 g of p-toluylic acid chloride was added to the solution while cooling with ice-water, and the resulting mixture was stirred for 1.5 hours at room temperature. The precipitate formed was separated by filtration, and washed successively with dimethylformamide and diethyl ether to obtain 4.2 g of 5-(1-hydroxy-2-isopropylaminobutyl)-8-p-methylbenzoyloxycarbostyril having a melting point of 197°-198° C. (after recrystallization from chloroform-diethyl ether).

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionthe resulting residue was dissolved in 100 ml of dimethylformamide
  3. addition3.0 g of p-toluylic acid chloride was added to the solution
  4. temperaturewhile cooling with ice-water
  5. customThe precipitate formed
  6. customwas separated by filtration
  7. washwashed successively with dimethylformamide and diethyl ether

Sources & evidence

ORD record
ord-6d5474d04144443dbbc59169da61ddb4
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Linked notes

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