Sodium → 8-(p-Chlorobenzoyloxy)-5-(1-hydroxy-2-benzylaminobutyl)carbostyril

HRID 27787Notes

Reaction equation

HRID 27787 reaction equation
[ClH:1].[OH:2][CH:3]([C:15]1[CH:24]=[CH:23][C:22]([OH:25])=[C:21]2[C:16]=1[CH:17]=[CH:18][C:19](=[O:26])[NH:20]2)[CH:4]([NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH3:6].[CH3:27][O-:28].[Na+].[Na]>CO>[Cl:1][C:9]1[CH:14]=[CH:13][C:12]([C:27]([O:25][C:22]2[CH:23]=[CH:24][C:15]([CH:3]([OH:2])[CH:4]([NH:7][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:5][CH3:6])=[C:16]3[C:21]=2[NH:20][C:19](=[O:26])[CH:18]=[CH:17]3)=[O:28])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 233420845-(1-Hydroxy-2-benzylaminobutyl)-8-hydroxycarbostyril hydrochloride

Product 1

HCID 233420588-(p-Chlorobenzoyloxy)-5-(1-hydroxy-2-benzylaminobutyl)carbostyril

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

1 g of 5-(1-hydroxy-2-benzylaminobutyl)-8-hydroxycarbostyril hydrochloride was suspended in 20 ml of methanol, and sodium methylate prepared from 135 mg of sodium metal and 2.8 ml of absolute methanol was added to the suspension. The mixture was then concentrated to dryness, and the resulting residue was dissolved in 10 ml of dimethylformamide. 490 mg of p-chlorobenzoyl chloride was then added dropwise to the mixture while cooling with ice-water. The mixture was then stirred for 1 hour, and water was added to the mixture. The mixture was then extracted with chloroform, and chloroform was removed by distillation. Diethyl ether was added to the residue to crystallize the product, and the crystals were separated by filtration, washed with diethyl ether and recrystallized from a mixture of chloroform and diethyl ether to obtain 110 mg of 8-(p-chlorobenzoyloxy)-5-(1-hydroxy-2-benzylaminobutyl)carbostyril having a melting point of 125°-126° C.

Workup

  1. additionwas added to the suspension
  2. concentrationThe mixture was then concentrated to dryness
  3. dissolutionthe resulting residue was dissolved in 10 ml of dimethylformamide
  4. addition490 mg of p-chlorobenzoyl chloride was then added dropwise to the mixture
  5. temperaturewhile cooling with ice-water
  6. additionwater was added to the mixture
  7. extractionThe mixture was then extracted with chloroform, and chloroform
  8. customwas removed by distillation
  9. additionDiethyl ether was added to the residue
  10. customto crystallize the product
  11. customthe crystals were separated by filtration
  12. washwashed with diethyl ether
  13. customrecrystallized from a mixture of chloroform and diethyl ether

Sources & evidence

ORD record
ord-35142690883b4061a88a7f561d01a7db
Source dataset
uspto-grants-1980_09
Patent number
US04223137

Reaction notes

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