Pyridine → 6-(4-benzoyloxypiperidino)-2(1H)-quinolinone

HRID 1085471Notes

Reaction equation

HRID 1085471 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]3)[CH2:4][CH2:3]1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.N1C=CC=CC=1.C(=O)(O)[O-].[Na+]>O>[C:19]([O:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13](=[O:18])[CH:12]=[CH:11]3)[CH2:4][CH2:3]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 104669946-(4-Hydroxypiperidino)carbostyril

Product 1

HCID 200601546-(4-benzoyloxypiperidino)-2(1H)-quinolinoneYield 50.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(4-hydroxypiperidino)carbostyril (0.25 g), benzoyl chloride (0.17 g) and dry pyridine (2 mL) was heated for 3 hours at 100° C. The reaction mixture was cooled and water (about 25 mL) and sodium bicarbonate (1 g) were added. The mixture was chilled in ice and stirred. The resulting solid was removed by filtration, washed with water and dried to give crude 6-(4-benzoyloxypiperidino)-2(1H)-quinolinone (0.25 g). Recrystallization twice from ethyl acetate gave 6-(4-benzoyloxypiperidino)-2(1H)-quinolinone (0.18 g); m.p. 212°-215° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe mixture was chilled in ice
  3. customThe resulting solid was removed by filtration
  4. washwashed with water
  5. customdried
  6. customto give crude 6-(4-benzoyloxypiperidino)-2(1H)-quinolinone (0.25 g)
  7. customRecrystallization twice from ethyl acetate

Sources & evidence

ORD record
ord-79fca90e596d4f16934f94a30d985071
Source dataset
uspto-grants-1991_04
Patent number
US05010088

Reaction notes

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