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

HRID 1085470Notes

Reaction equation

HRID 1085470 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](OC(=O)C)(=[O:21])[CH3:20].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:21])[CH3:20]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 104669946-(4-Hydroxypiperidino)carbostyril

Product 1

HCID 200601526-(4-acetoxypiperidino)-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 6-(4-hydroxypiperidino)carbostyril (0.25 g), acetic anhydride (0.4 g) and dry pyridine (4 mL) was heated at 100° C. for 3 hours. The reaction mixture was cooled and water (about 35 mL) and sodium bicarbonate (0.6 g) were added. The mixture was chilled in ice and stirred. The resulting white solid was removed by filtration, washed with water and dried to give 6-(4-acetoxypiperidino)-2(1H)-quinolinone. 1/4 hydrate (0.3 g); m.p. 245°-250° C.

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperatureThe mixture was chilled in ice
  3. customThe resulting white solid was removed by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b80b82fe7d2a4a3ebf85b1138c3e9ab5
Source dataset
uspto-grants-1991_04
Patent number
US05010088

Reaction notes

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