Peracetic Acid → 7-(Ethoxycarbonyl)quinoline 1-oxide

HRID 2403695Notes

Reaction equation

HRID 2403695 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C(OO)(=[O:18])C>ClCCl>[CH2:14]([O:13][C:11]([C:8]1[CH:9]=[C:10]2[C:5]([CH:4]=[CH:3][CH:2]=[N+:1]2[O-:18])=[CH:6][CH:7]=1)=[O:12])[CH3:15]

Participants

4

Reactant 2

HCID 6585Peracetic AcidHCID 3799493Ethyl Quinoline-7-carboxylate

Product 1

HCID 674915557-(Ethoxycarbonyl)quinoline 1-oxideYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl quinoline-7-carboxylate (1.02 g, 5.05 mmol) in dichloromethane (20 mL) was added peracetic acid (2.13 mL, 10.1 mmol, 32 wt % in acetic acid). The reaction was stirred at room temperature overnight. The reaction was partitioned between water and dichloromethane. The layers were separated and the aqueous was extracted with dichloromethane (4×). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated. The solid was concentrated from heptanes and ethyl acetate several times, then dried under vacuum to give the title compound (1.01 g, 92%) as a yellow solid. +ESI (M+H) 218.2; 1H NMR (400 MHz, CDCl3, δ): 9.40 (s, 1 H), 8.65 (d, J=6.05 Hz, 1 H), 8.27 (dd, J=8.58, 1.56 Hz, 1 H), 7.95 (d, J=8.39 Hz, 1 H), 7.82 (d, J=8.58 Hz, 1 H), 7.42 (dd, J=8.49, 6.15 Hz, 1 H), 4.47 (q, J=7.02 Hz, 2 H), 1.45 (t, J=7.1 Hz, 3 H).

Workup

  1. customThe reaction was partitioned between water and dichloromethane
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with dichloromethane (4×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. concentrationThe solid was concentrated from heptanes and ethyl acetate several times
  9. customdried under vacuum

Sources & evidence

ORD record
ord-8d96686cb6544eb1a692eb02989f2b20
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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