5-[2-(ethylamino)-1-hydroxybutyl]-8-hydroxyquinolin-2(1h)-one → HCID 23342049, compound

HRID 27786Notes

Reaction equation

HRID 27786 reaction equation
[OH:1][CH:2]([C:9]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]2[C:10]=1[CH:11]=[CH:12][C:13](=[O:20])[NH:14]2)[CH:3]([NH:6][CH2:7][CH3:8])[CH2:4][CH3:5].[CH3:21][O-:22].[Na+].[Na]>CO>[CH:9]1([CH2:2][CH2:3][C:21]([O:19][C:16]2[CH:17]=[CH:18][C:9]([CH:2]([OH:1])[CH:3]([NH:6][CH2:7][CH3:8])[CH2:4][CH3:5])=[C:10]3[C:15]=2[NH:14][C:13](=[O:20])[CH:12]=[CH:11]3)=[O:22])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:10]1

Participants

5

Reactant 3

HCID 1915345-[2-(ethylamino)-1-hydroxybutyl]-8-hydroxyquinolin-2(1h)-oneHCID 5360545SodiumHCID 10942334Sodium Methoxide

Product 1

HCID 23342049HCID 23342049, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

5 g of 5-(1-hydroxy-2-ethylaminobutyl)-8-hydroxycarbostyril was suspended in 20 ml of methanol, and sodium methylate prepared from 458 mg of sodium metal and 9.6 ml of absolute methanol was added to the suspension. The mixture was then concentrated to dryness, and the resulting residue was dissolved in 30 ml of dimethylformamide. 3.3 g of β-cyclohexylpropionyl chloride was then added dropwise to the mixture while cooling with ice-water. The mixture was then stirred for 1 hour at room temperature, and diethyl ether was added to the mixture. The precipitate formed was separated by filtration, washed with diethyl ether and recrystallized from a mixture of methanol and diethyl ether to obtain 3.86 g of 8-(β-cyclohexylpropionyloxy)-5-(1-hydroxy-2-ethylaminobutyl)carbostyril having a melting point of 233°-234° C. (with decomposition).

Workup

  1. additionwas added to the suspension
  2. concentrationThe mixture was then concentrated to dryness
  3. dissolutionthe resulting residue was dissolved in 30 ml of dimethylformamide
  4. addition3.3 g of β-cyclohexylpropionyl chloride was then added dropwise to the mixture
  5. temperaturewhile cooling with ice-water
  6. additiondiethyl ether was added to the mixture
  7. customThe precipitate formed
  8. customwas separated by filtration
  9. washwashed with diethyl ether
  10. customrecrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-3820b6822e95465792c5e3356e2cc4d0
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

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