Pyridine → HCID 13236317, compound

HRID 1649215Notes

Reaction equation

HRID 1649215 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.N1C=CC=CC=1.CN(C=O)C.[N+:29]([C:32]1[CH:40]=[CH:39][C:35]([C:36](Cl)=[O:37])=[CH:34][CH:33]=1)([O-:31])=[O:30]>O>[N+:29]([C:32]1[CH:33]=[CH:34][C:35]([C:36]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]4)[CH2:2][CH2:3]2)=[O:37])=[CH:39][CH:40]=1)([O-:31])=[O:30]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228Dimethylformamide2×HCID 85024-Nitrobenzoyl chlorideHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 13236317HCID 13236317, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-(1-Piperazinyl)-3,4-dihydrocarbostyril (2.6 g) and 2 ml of pyridine were added to 40 ml of DMF. The mixture was stirred at room temperature while slowly adding dropwise 10 ml of DMF solution containing 2.7 g of 4-nitrobenzoyl chloride. After completion of addition, the reaction mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into a large amount of water and extracted with chloroform. The extract was washed with sodium hydrogencarbonate solution and subsequently with water and dried over anhydrous sodium sulfate. Chloroform was distilled off and residual crystals were recrystallized from methanol-chloroform to give 2.4 g of 6-[4-(4-nitrobenzoyl)-1-piperazinyl]-3,4-dihydrocarbostyril, m.p. 235.5°-236.5° C.

Workup

  1. additionAfter completion of addition
  2. stirringthe reaction mixture was stirred at the same temperature for 30 minutes
  3. extractionextracted with chloroform
  4. washThe extract was washed with sodium hydrogencarbonate solution and subsequently with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationChloroform was distilled off
  7. customresidual crystals were recrystallized from methanol-chloroform

Sources & evidence

ORD record
ord-73c2a461b1f944e58fbed850315aa81a
Source dataset
uspto-grants-1983_11
Patent number
US04415572

Reaction notes

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