m-Chloroperbenzoic acid → 6-(Ethoxycarbonyl)quinoline 1-oxide

HRID 711074Notes

Reaction equation

HRID 711074 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.ClC1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[CH2:14]([O:13][C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N+:1]([O-:21])=[CH:2][CH:3]=[CH:4]2)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 946706-Quinolinecarboxylic acid, ethyl ester

Product 1

HCID 669781646-(Ethoxycarbonyl)quinoline 1-oxideYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To ethyl quinoline-6-carboxylate (3.2 g, 16 mmol) in dichloromethane (120 mL) was added meta-chloroperoxybenzoic acid (4.9 g, 0.024 mol) portionwise. The reaction was stirred at room temperature for 4 hours. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium carbonate (3×30 mL) and brine (2×40 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave the title compound (2.45 g, 71%) as a brown solid. 1H NMR (400 MHz, CDCl3, δ): 8.81-8.79 (d, 1H), 8.62 (s, 2H), 8.35-8.33 (d, 1H), 7.87-7.85 (d, 1H), 7.39 (s, 1H), 4.49-4.44 (q, 2H), 1.47-1.43 (t, 3H).

Workup

  1. washwashed with saturated aqueous sodium carbonate (3×30 mL) and brine (2×40 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-bca6e842f79a4374b94b90d1f960b3e8
Source dataset
uspto-grants-2015_11
Patent number
US09181252B2

Reaction notes

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