Piperidine → 4(1H)-Quinolinone, 3-hydroxy-1-methyl-

HRID 358656Notes

Reaction equation

HRID 358656 reaction equation
C([O:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[CH:11]=1)(=O)C1C=CC=CC=1.N1CCCCC1>ClCCl>[OH:9][C:10]1[C:19](=[O:20])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:21])[CH:11]=1

Participants

4

Reactant 2

HCID 8082Piperidine2×HCID 539443861-Methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate

Product 1

HCID 5900784(1H)-Quinolinone, 3-hydroxy-1-methyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-methyl-4-oxo-1,4-dihydroquinol-3-yl benzoate (45 g), piperidine (16.9 ml) and dichloromethane (700 ml) was stirred for 3 days at ambient temperature under nitrogen. A further portion of piperidine (3 ml) was added and the stirring continued for 1 day. The solvent was removed by distillation at 50° and the residue was triturated with diethyl ether (300 ml). The resultant solid was collected by filtration and washed with diethyl ether (2×100 ml) to give 3-hydroxy-1-methyl-4-quinolone, m.p. 243°-246°.

Workup

  1. waitthe stirring continued for 1 day
  2. customThe solvent was removed by distillation at 50°
  3. customthe residue was triturated with diethyl ether (300 ml)
  4. filtrationThe resultant solid was collected by filtration
  5. washwashed with diethyl ether (2×100 ml)

Sources & evidence

ORD record
ord-30ebf9365b414b4e96b9d8680104048a
Source dataset
uspto-grants-1991_03
Patent number
US04997840

Reaction notes

Loading…