m-Chloroperbenzoic acid → 1-[1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-oxo-1,4-dihydroquinolin-7-yl]piperidine 1-oxide monohydrate

HRID 542822Notes

Reaction equation

HRID 542822 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:10]=2)[C:5](=[O:18])[C:4]([C:19]2[N:23]([CH3:24])[N:22]=[N:21][N:20]=2)=[CH:3]1.ClC1C=CC=C(C(OO)=[O:33])C=1.C(=O)(O)[O-].[Na+]>ClCCl>[OH2:18].[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:12]3([O-:33])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]3)[CH:10]=2)[C:5](=[O:18])[C:4]([C:19]2[N:23]([CH3:24])[N:22]=[N:21][N:20]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acid2×HCID 516892Sodium BicarbonateHCID 134744311-methyl-3-(1-methyl-1H-tetrazol-5-yl)-7-piperidino-4-quinolone

Product 1

HCID 202072491-[1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-oxo-1,4-dihydroquinolin-7-yl]piperidine 1-oxide monohydrate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of the 4-quinolone of Example 30 (1.44 g) in dichloromethane (100 ml) was added a solution of 3-chloroperbenzoic acid (85%, 0.86 g) in dichloromethane (20 ml) and the mixture was stirred for 52 hours. A solution of 3-chloroperbenzoic acid (85%, 0.27 g) in dichloromethane (10 ml) was added and the mixture was stirred for 20 hours. Saturated aqueous sodium bicarbonate (40 ml) was added and the mixture was stirred for 45 minutes. The mixture was evaporated to dryness and the residue was extracted with dichloromethane (75 ml) for 1.5 hours using a Soxhlet apparatus. The extract was evaporated and the residue was crystallised from industrial methylated spirit:diethyl ether 4:1 to give 1-[1-methyl-3-(1-methyl-1H-tetrazol-5-yl)-4-oxo-1,4-dihydroquinolin-7-yl]piperidine 1-oxide monohydrate, m.p. 163°-166°.

Workup

  1. stirringthe mixture was stirred for 20 hours
  2. stirringthe mixture was stirred for 45 minutes
  3. customThe mixture was evaporated to dryness
  4. extractionthe residue was extracted with dichloromethane (75 ml) for 1.5 hours
  5. customThe extract was evaporated
  6. customthe residue was crystallised from industrial methylated spirit:diethyl ether 4:1

Sources & evidence

ORD record
ord-474c1567ab174990867c79ae30cc4a6f
Source dataset
uspto-grants-1987_04
Patent number
US04659718

Reaction notes

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