Dimethylformamide → 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]-2-propenyloxy}carbostyril

HRID 1903186Notes

Reaction equation

HRID 1903186 reaction equation
CN(C)C=O.[OH:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2.C([O-])([O-])=O.[K+].[K+].[CH:24]1([N:30]([CH2:37][CH2:38][OH:39])[C:31](=[O:36])/[CH:32]=[CH:33]/[CH2:34]Br)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1>O>[OH:39][CH2:38][CH2:37][N:30]([CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]1)[C:31]([CH:32]=[CH:33][CH2:34][O:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH:11]=[CH:10]2)=[O:36]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1770652,6-DihydroxyquinolineHCID 20468037N-cyclohexyl-N-(2-hydroxyethyl)-gamma-bromocrotonamide

Product 1

HCID 537953026-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]-2-propenyloxy}carbostyrilYield 73.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 200 ml of N,N-dimethylformamide and 50 ml of water was added 16 g of 6-hydroxycarbostyril and 17 g of K2CO3, while the mixture was stirred at a room temperature, 31 g of N-cyclohexyl-N-(2-hydroxyethyl)-γ-bromocrotonamide was added dropwise. After the addition the reaction mixture was stirred for 3 hours and was concentrated. To the residue thus obtained 500 ml of chloroform was added and washed with water, a dilueted NaOH aqueous solution and water. The organic layer was concentrated. The residue thus obtained was recrystallized from methanol-water to obtain 27 g of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]-2-propenyloxy}-carbostyril as in the form of colorless needle-like crystals. The chemical structure of this substance was identified by the NMR spectrum and the data of elementary analysis.

Workup

  1. additionAfter the addition the reaction mixture
  2. stirringwas stirred for 3 hours
  3. concentrationwas concentrated
  4. additionTo the residue thus obtained 500 ml of chloroform was added
  5. washwashed with water
  6. concentrationThe organic layer was concentrated
  7. customThe residue thus obtained
  8. customwas recrystallized from methanol-water

Sources & evidence

ORD record
ord-e5ef47d9a12843dc9147b235148480fe
Source dataset
uspto-grants-1984_03
Patent number
US04435404

Reaction notes

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